Acetic anhydride (Ac2O), All Preps (501) for Substance (1) by Asch

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2016-05-09 22h:45m:25s (EST)

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Rx-ID: 5589278 View in Reaxys 1/501 Yield 95%

Conditions & References 31 : Example 31 The acetic anhydride yield was more than 95percent based on the methyl acetate. Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; EP636599; (1995); (A1) English View in Reaxys

83.2%

16 : Reagent: acetic anhydride Reagent: acetic anhydride Yield: 83.2percent 1H Nuclear Magnetic Resonance Spectrum (400 MHz, CDCl ) δ ppm: 3 7.44 (2H, doublet, J=8.3 Hz); 7.22 (2H, doublet, J=8.3 Hz); Patent; SANKYO COMPANY, LIMITED; US2003/139601; (2003); (A1) English View in Reaxys

62.5%

XXXI : Preparation of compound 9 and conversion thereof with acetic anhydride into 1,1,1-trichloro-3-methyl-2-butyl acetate EXAMPLE XXXI Preparation of compound 9 and conversion thereof with acetic anhydride into 1,1,1-trichloro-3-methyl-2-butyl acetate A 100-ml flask was charged with trichloroacetic acid (0.10 mol) and N,N-dimethylformamide (25 ml) and then with potassium fluoride (0.12 mol), which caused the temperature to rise from 20° to 55° C. with vigorous evolution of carbon dioxide. After cooling to 28° C. isobutyraldehyde (0.09 mol) was added, which caused the temperature to rise to 36.5° C. after 15 minutes. At this moment conversion of isobutyraldehyde was 50percent and the selectivity to 1,1,1-trichloro-3-methyl-2-butaTol 100percent. Then, acetic anhydride (0.12 mol) was added, which caused the temperature to rise from 22° to 41° C. within 35 minutes. As the mixture obtained was difficult to stir it was heated to 80° C. and stirred at this temperature for 30 minutes. The mixture was cooled to 60° C., water (10 ml) was added and the mixture was allowed to adopt a temperature of 20° C. Then, the mixture was taken up in n-pentane (50 ml), the solution obtained was washed with three portions of 30 ml water, the washed solution was dried and the n-pentane was evaporated from the dried solution to give a residue (14.7 g) of the title acetate, the yield thereof being 62.5percent. Patent; Shell Oil Company; US4285882; (1981); (A1) English View in Reaxys

61.1%

21 : EXAMPLE 21 EXAMPLE 21 The reaction was carried out according to the method described in Example 1 except using a mixture (37.9 g) of 78:22 (wt. percent) methyl acetate-methanol as a material to be carbonylated and no addition of acetic acid, and the reaction time of 90 minutes. The results were as follows: conversion of methanol, 100percent; conversion of methyl acetate, 61.1percent: yield of acetic acid, 267.0 mmol; yield of acetic anhydride, 244.4 mmol. Patent; Daicel Chemical Industries, Ltd.; US4603020; (1986); (A1) English View in Reaxys zur Durchfuehrung dieses Verfahrens in der Technik Nicodemus in K.Winnacker;E.Weingaertner; View in Reaxys Sixt; ; vol. 6; (1955); p. 810 - 812 View in Reaxys Benson; ; vol. 1; (1947); p. 83 - 85 View in Reaxys

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Ellis,J. et al.; Australian Journal of Chemistry; vol. 24; (1971); p. 1527 - 1529 View in Reaxys Yates,P.; Hambly,G.F.; Canadian Journal of Chemistry; vol. 57; (1979); p. 1668 - 1678 View in Reaxys Martin,D.; Chemische Berichte; vol. 98; (1965); p. 3286 - 3296 View in Reaxys Taylor,E.C. et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 2422 - 2423 View in Reaxys Munoz,A. et al.; Bulletin de la Societe Chimique de France; (1971); p. 1424 - 1436 View in Reaxys Aida,T. et al.; Chemistry Letters; (1975); p. 29 - 32 View in Reaxys Mukaiyama,T. et al.; Journal of Organic Chemistry; vol. 33; nb. 6; (1968); p. 2242 - 2245 View in Reaxys Pudovik,A.N. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; nb. 8; (1960); p. 2624 - 2630,2606 - 2612 View in Reaxys Schwarz,S.; Weber,G.; Journal fuer Praktische Chemie (Leipzig); vol. 312; (1970); p. 653 - 659 View in Reaxys Martin et al.; Angewandte Chemie; vol. 77; (1965); p. 96 View in Reaxys Oae et al.; Chemical and Pharmaceutical Bulletin; vol. 23; (1975); p. 3011,3013 View in Reaxys Doumaux et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 3992 View in Reaxys Ho; Wong; Synthetic Communications; vol. 3; (1973); p. 63,64 View in Reaxys Jones; Ritchie; Journal of the Chemical Society; (1960); p. 4141,4151 View in Reaxys Dutka; Marton; Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,; vol. 24; (1969); p. 1664 View in Reaxys Jeffery; Satchell; Journal of the Chemical Society; (1962); p. 1876 View in Reaxys Jeffery; Satchell; Chemistry and Industry (London, United Kingdom); (1960); p. 1444 View in Reaxys Jakobson; Zhurnal Vsesoyuznogo Khimicheskogo Obshchestva im. D. I. Mendeleeva; vol. 5; (1960); p. 708,709 View in Reaxys Henry; Journal of Organic Chemistry; vol. 38; (1973); p. 3596,3600 View in Reaxys Susuki et al.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 2663 View in Reaxys Kamai et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 41; (1971); p. 1285,1294 View in Reaxys Weinshenker; Shen; Tetrahedron Letters; (1972); p. 3281,3282, 3283 View in Reaxys Nifant'ev; Fursenko; J. Gen. Chem. USSR (Engl. Transl.); vol. 39; (1969); p. 1028,999,1000,1002 View in Reaxys Mukaiyama et al.; Journal of Organic Chemistry; vol. 28; (1963); p. 2024,2026 View in Reaxys Adduci; Ramirez; Organic Preparations and Procedures; vol. 2; (1970); p. 321,323 View in Reaxys Swetlakow et al.; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 2246,2183 View in Reaxys Dubrovin et al.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 22; (1977); p. 882,884 View in Reaxys Cicolella et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 268; (1969); p. 1929 View in Reaxys 11 : EXAMPLE 11 EXAMPLE 11

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Experiment P was repeated except that 5percent w/w formic acid was also charged to the reaction feed tank. The carbonylation rate was found to be 12.9 mol/l/hr whilst the level of ethylidene diacetate in the product acetic acid/acetic anhydride was 413 ppm. Patent; Allan, Robert Edward; Watson, Derrick John; US2001/7912; (2001); (A1) English View in Reaxys 3 : Reference Example 3 Reference Example 3 In the same manner as in Example 3, a ketene obtained by thermal decomposition of acetic acid through a ketene furnace was absorbed in acetic acid to obtain crud acetic anhydride, this crude acetic anhydride was subjected to ozone treatment. Patent; Nishioka, Seiji; Maeda, Ryosuke; Fukui, Toshifumi; Yamashira, Mitsuru; US2001/29309; (2001); (A1) English View in Reaxys 4 : Example 4 Example 4 Acetic anhydride was produced in the same manner as in Example 3 except that the amount of the ozonized air introduced in the packed column 2in ozone treatment was 120 NL/H in the process of producing acetic anhydride in Example 3. The resulted crude acetic anhydride had a purity of 99.5percent, the total content of dissolved ozone and the ozonization intermediate was 124 ppm in terms of ozone, and of this content, the content of the ozonization intermediate was 112 ppm. Patent; Nishioka, Seiji; Maeda, Ryosuke; Fukui, Toshifumi; Yamashira, Mitsuru; US2001/29309; (2001); (A1) English View in Reaxys 9 : EXAMPLE 9 EXAMPLE 9 Experiment O was repeated except that formic acid (5percent w/w) was added to the feed to the reactor. The rate of carbonylation was found to be 12.8 mol/l/hr and the ethylidene diacetate level was found to be 1020 ppm in the product acetic acid/acetic anhydride. Patent; Allan, Robert Edward; Watson, Derrick John; US2001/7912; (2001); (A1) English View in Reaxys 10 : EXAMPLE 10 Analysis of the gases vented from the autoclave, by gas chromatography, showed that 0.58 mmoles of methane and 4.06 mmol carbon dioxide had been formed during the reaction. This Example is according to the present invention and demonstrates the benefit of the presence of ruthenium in the liquid reaction composition on the carbonylation rate of methyl acetate under substantially anhydrous conditions to produce acetic anhydride. Patent; BP Chemicals Limited; US5939585; (1999); (A1) English View in Reaxys 12 : 10a. Similarly, from the reaction of 5-methyl-2-(4-aminophenyl)-2,4-dihydro-pyrazol-3-one (synthesised as in Example 10) and acetic anhydride is obtained N-(4-phenyl(4,5-dihydro-3-methyl-5-oxo-5H-pyrazol-1-yl))-acetamide. Patent; Cell Pathways, Inc.; US6034099; (2000); (A1) English View in Reaxys II : ACETIC ANHYDRIDE TREATMENT OF PRODUCT (MELT) EXAMPLE II ACETIC ANHYDRIDE TREATMENT OF PRODUCT (MELT) The Primary Reaction is run at 85° C. for 5 hours with vacuum applied during the second half to remove most of the solvent. This gives Sample A. Acetic anhydride is added to the polyhydroxy fatty acid amide amidation product (fluid melt), with stirring, allowed to exotherm to 100° C., and maintained at 85° C. for an additional 30 minutes. This gives Sample B.

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The reaction mixture is poured into water to give a solution at pH 4.9. Sodium hydroxide and hydrogen chloride are added with stirring to reach and maintain pH 7.3. This gives Sample C. A portion of Sample C is bottled and allowed to stand at room temperature over the weekend. This gives Sample D. Patent; The Procter and Gamble Company; US5298636; (1994); (A1) English View in Reaxys 16 : EXAMPLE 16 EXAMPLE 16 Into a three-necked flask equipped with a thermometer, a distillation column, a reflux condenser, a cooler and a separator are introduced salicylic aldehyde (600 mmole) prepared according to the previous example and recovered by distillation and acetic anhydride (1.90 mmole) dissolved in acetic acid (3.47 g). Patent; Rhone-Poulenc Chimie; US5334769; (1994); (A1) English View in Reaxys 3 : EXAMPLE 3 EXAMPLE 3 The heterogeneous rhodium catalyst formed in Example 1 or insitu via addition of, for example, RhI3 with crosslinked polyvinylpyrrolidone and methyl iodide (MeI), methyl acetate (MeAc) and acetic acid (HAc) was used to produce acetic anhydride. Patent; Hoechst Celanese Corporation; US5466874; (1995); (A1) English View in Reaxys iii : C. The product is benzoylated with benzoic anhydride and pyridine to obtain 16 which can be acetylated with acetic anhydride under strongly acidic conditions, preferably a mixture of acetic acid and concentrated sulfuric acid, to provide the desired product 17. Patent; Gensia, Inc.; US5506347; (1996); (A1) English View in Reaxys p.5 : EXAMPLE P6 STR17 8.3 g of 2-morpholino-5-formylthiazole and 13.6 g of the compound of the formula STR18 were dissolved in 100 ml of methylene chloride. After 100 ml of acetic anhydride had been added, the methylene chloride was distilled off and the temperature was increased to 120° C. After cooling to 100° C. with stirring, the target product precipitated. Following addition of 100 ml of methanol, the mixture was stirred overnight and filtered with suction, and the filter residue was washed with methanol and dried. Yield: 17.1 g=76percent of theory Melting point: >210° C. λmax (THF): 531 nm Rf: 0.45 (ethyl acetate) Example P6 was also followed to synthesize the following dyes: Patent; BASF Aktiengesellschaft; US5079365; (1992); (A1) English View in Reaxys 11 : EXAMPLE 11 EXAMPLE 11 The reaction was carried out according to the method described in Example 5 except using Rh4 (CO)12 (1.29 mg atom Rh) as a rhodium catalyst and doubling the volume of methyl iodide (9.8 ml). The yield of acetic anhydride in the reaction liquid (81 ml) was 459.4 mmol and, besides, acetyl iodide (5.5 mmol) was observed. Patent; Daicel Chemical Industries, Ltd.; US4603020; (1986); (A1) English View in Reaxys 19 : EXAMPLE 19 EXAMPLE 19

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The reaction was carried out according to the method described in Example 1 except using Rh4 (CO)12 (0.115 g) instead of RhCl3.3H 2 O. The results were as follows: conversion of methyl acetate 84.4percent; yield of acetic anhydride 337.22 mmol; reaction rate, 546 mol/mol Rh*hr. Patent; Daicel Chemical Industries, Ltd.; US4603020; (1986); (A1) English View in Reaxys 1 : EXAMPLE 1 EXAMPLE 1 RhCl3.3H 2 O (0.163 g), methyl iodide (14.2 g), Aluminum powder (0.2 g), acetic acid (10.2 g) and methyl acetate (29.1 g) were charged into a 300-ml Hastelloy autoclave. The air in the autoclave was replaced by carbon monoxide and the pressure was increased to 40 kg/cm2 G with carbon monoxide. The autoclave was heated to 175° C., when the reaction was initiated and continued for 60 minutes after gas absorption was observed. After the completion of the reaction, the autoclave was cooled, the residual pressure was discharged, and the reaction liquid was take up and analyzed by gas chromatography. The results were as follows: conversion of methyl acetate, 88.7percent; yield of acetic anhydride, 348.3 mmol; reaction rate, 569.1 mol/mol Rh*hr. Patent; Daicel Chemical Industries, Ltd.; US4603020; (1986); (A1) English View in Reaxys 3 : (comparative) EXAMPLE 3 (comparative) The reaction was carried out according to the method described in Example 1 except changing the charge of methyl acetate (38.5 g) and no addition of acetic acid. The results were as follows: conversion of methyl acetate, 51.4percent; yield of acetic anhydride, 267.3 mmol; reaction rate, 431 mol/mol Rh*hr. Patent; Daicel Chemical Industries, Ltd.; US4603020; (1986); (A1) English View in Reaxys 4 : EXAMPLE 4 EXAMPLE 4 The reaction was carried out according to the method described in Example 1 except using propionic acid (10.1 g) instead of acetic acid. The results were as follows: conversion of methyl acetate, 88.6percent; yield of acetic anhydride, 272.6 mmol; yield of propionic anhydride, 69.0 mmol. The reaction rate calculated based on the gas absorption was 527 mol/mol Rh*hr. Patent; Daicel Chemical Industries, Ltd.; US4603020; (1986); (A1) English View in Reaxys (Reaction) The rate of reaction in terms of a rate of formation of acetic anhydride per one mol of rhodium was 345.1 mol/mol Rh*hr. No ethylidene diacetate was formed. Patent; Daicel Chemical Industries, Ltd.; US4735749; (1988); (A1) English View in Reaxys 1 : EXAMPLE 1 EXAMPLE 1 Acetic formic anhydride was prepared (but not isolated) by heating a mixture of 30 ml of acetic anhydride and 14.5 ml of 90percent formic acid for two hours at 50°-60° C. To the mixture cooled to room temperature was added portionwise with stirring 15.0 g of 2-amino-5-ethoxy-carbonyl-4,6-dimethylbenzoic acid. Stirring was continued for another two hours and the mixture was poured into ice water. The resulting precipitates were filtered and air dried to yield 14.2 g of a crystalline solid. Patent; Ishikawa; Masayuki; US4276295; (1981); (A1) English

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View in Reaxys 33 : 1-Methyl-3-acetoxy-5-(2-chlorophenyl)-6-aza-7-chloro-1,2-dihydro-3H-1,4-benzo-diazepinone-(2) STR41 21 grams of 1-methyl-5-(2-chloro-phenyl)-6-aza-7-chloro-1,2-dihydro-3H-1,4-benzodiazepinone-(2)-4-oxide were heated for 15 minutes at the boiling point with stirring in a mixture of 33 ml of acetic anhydride and 29 ml of glacial acetic acid. EXAMPLE 33 1-Methyl-3-acetoxy-5-(2-chlorophenyl)-6-aza-7-chloro-1,2-dihydro-3H-1,4-benzo-diazepinone-(2) STR41 21 grams of 1-methyl-5-(2-chloro-phenyl)-6-aza-7-chloro-1,2-dihydro-3H-1,4-benzodiazepinone-(2)-4-oxide were heated for 15 minutes at the boiling point with stirring in a mixture of 33 ml of acetic anhydride and 29 ml of glacial acetic acid. After cooling and inoculation (seeding) the desired material crystallized out. It was washed with glacial acetic acid and then with water. M.P. 178° to 179° C. Patent; Deutsche Gold- und Silber-Scheideanstalt vormals Roessler; US31071; (1982); (E1) English View in Reaxys 4.12 : EXAMPLE 4 (12) Starting from a mixture of 2-ethoxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3carboxylate (900 mg), hydroxylamine hydrochloride (167 mg) and sodium acetate (341 mg) in acetic acid (7 ml) and acetic anhydride (1 ml) was obtained by applying an essentially similar manner to that of Example 4-(2), crystals (420 mg) of 2-ethoxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-cyano-1,4-dihydropyridine-3-carboxylate, m.p. 129° to 130.5° C. (recrystallized from a mixture of diethyl ether and n-hexane). Patent; Fujisawa Pharmaceutical Co., Ltd.; US4284634; (1981); (A1) English View in Reaxys 5 : EXAMPLE 5 EXAMPLE 5 280 g methyl acetate, 1.8 g IrCl3, 8 g ZrOCl2.8H 2 O, 60 g CH3 I, 50 g acetic acid and 100 g N-methyl-quinolinium iodide were placed in a Hastelloy autoclave and reacted therein with CO at 465 K. under 80 bars. After 38 minutes, analysis indicated the formation of 273 g acetic anhydride, corresponding to 372 g Ac2 O per g Ir per hour. Patent; Hoechst Aktiengesellschaft; US4333884; (1982); (A1) English View in Reaxys 6 : Thiazole-2-azo-4'-(1'-acetoxynaphthalene) 2.55 g. (0.01 mol) 4-(2'-Thiazolylazo)-1-naphthol are heated to 80° C. for 1 hour with 100 ml. acetic anhydride, to which 1 ml. pyridine has been added. Thereafter, excess acetic anhydride and the acetic acid formed are substantially distilled off in a vacuum and 50 ml. methanol are added to the distillation residue, followed by complete evaporation to dryness. The residue is recrystallized from 15 ml. toluene to give 2.0 g. (67percent of theory) thiazole-2-azo-4'-(1'-acetoxynaphthalene) in the form of bright brown crystals; m.p. 137° C. Patent; Boehringer Mannheim GmbH; US4442033; (1984); (A1) English View in Reaxys 6 : EXAMPLE 6 EXAMPLE 6 To a mixture of 40 g of 2-hydroxy-6-methyl-4-pyrimidinecarbaldoxime and 400 ml of water was added 120 g of stannous chloride hydrate in 400 ml of concentrated hydrochloric acid. The mixture was stirred for about sixteen hours at 20° C. Partial evaporation provided a residue which was mixed with 120 ml of acetic anhydride and 10 g of sodium acetate. Patent; Riker Laboratories, Inc.; US4473570; (1984); (A1) English View in Reaxys 2 : Preparation of acetic anhydride: hydrogen absent EXAMPLE 2 Preparation of acetic anhydride: hydrogen absent Dimethyl ether (2.1 g), acetic acid (40 g), Co2 (CO)8 (0.4 g), methyl p-toluenesulphonate (12 g), N-methylimidazole (4 g) and sodium iodide (0.5 g), iodide:cobalt atomic ratio 1.5:1, were charged to a stainless steel autoclave which was pressured to 1200 psig with CO at room temperature. The vessel was then heated and stirred for one hour at 150° C.

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At this temperature the initial pressure was 1400 psig. Analysis of the reaction product mixture by gas chromatography (G.C.) showed it to contain 1.5 g of methyl acetate and 1.7 g of the acetic anhydride. Patent; BP Chemicals Limited; US4534912; (1985); (A1) English View in Reaxys 3 : Preparation of acetic anhydride: hydrogen absent EXAMPLE 3 Preparation of acetic anhydride: hydrogen absent A stainless steel autoclave was charged with a mixture of methyl acetate (35 g), acetic acid (15 g), Co2 (CO)8 (0.4 g), methyl p-toluenesulphonate (12 g), N-methylimidazole (5.3 g) and sodium iodide (0.5 g), iodide:cobalt atomic ratio 1.5:1. CO (1100 psig) was then added to the autoclave at room temperature. The vessel was heated and stirred for one hour at 150° C. At this temperature the initial pressure in the reactor was 1300 psig. Patent; BP Chemicals Limited; US4534912; (1985); (A1) English View in Reaxys 4 : EXAMPLE 4 EXAMPLE 4 Example 3 was repeated, using 32 millimols of methyl iodide, a solution of 1 millimol of methyltriphenylphosphonium tetracarbonylcobaltate in 40 ml of glyme, and 32 millimols of sodium acetate, carbon monoxide being bubbled therethrough (r=1). This provided 1.5 millimols of acetic anhydride, the same being a yield on the order of 5percent relative to either one of the reactants introduced. Patent; Rhone-Poulenc Chimie de Base; US4500473; (1985); (A1) English View in Reaxys 7 : EXAMPLE 7 EXAMPLE 7 The quantities of feed materials and reaction time were as in Example 6 but 5 g (0.03 mol) tetramethyl titanate was substituted for the 5 g tetrabutyl titanate. The acetic anhydride obtained was worked up distillatively and then subjected to gas-chromatographic analysis. 165 g corresponding to a yield of 1753 g (CH3 CO)2 O per liter reaction solution per hour was obtained. Patent; Hoechst Aktiengesellschaft; US4497747; (1985); (A1) English View in Reaxys I : EXAMPLE I EXAMPLE I Examples I through VIII illustrate the process of this invention for producing acetic anhydride by carbonylation of methyl acetate in the presence of a bimetallic catalyst. In Example I a glass liner was charged with 0.19 g (1.0 mmole) of hydrated ruthenium(IV) dioxide, 3.4 g (10 mmoles) of tetra-nbutylphosphonium bromide, 0.34 g (1 mmole) of dicobalt octacarbonyl and 10 ml of methyl acetate. The glass liner was placed in a stainless steel reactor. The reactor was purged of air and pressured to 2000 psi with carbon monoxide then was heated to 220° C. while it was agitated by rocking. The pressure was brought up to 5690 psi and constant pressure was maintained by repressuring from a surge tank. The reaction was stopped after 18 hours and the reactor cooled to room temperature. An off-gas sample was taken and excess gas vented from the reactor following which 13.9 g of dark brown product was recovered. Analysis of the liquid product by glc showed the presence of: 28percent MeOAc, 0percent HOAc and 46percent (CH3 CO)2 O. The methyl acetate conversion was calculated to be 72percent and acetic anhydride selectivity was 64percent. This example illustrates a process for producing acetic anhydride without using iodide promoter. Patent; Texaco Inc.; US4519956; (1985); (A1) English View in Reaxys

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V : EXAMPLE V EXAMPLE V In the manner described in Example I, 25 ml methyl acetate were carbonylated at 165° C. in the presence of 2 mmol NiCl2.6H 2 O, 15 mmol CH3 I, 15 mmol LiI.2H2 O, 25 ml sulfolane and 12 mmol triphenylphosphine oxide. The partial CO and H2 pressures before the autoclave was heated each measured 20 bar. After a reaction time of 3 hours the reaction mixture was analyzed with the aid of gas-liquid chromatography. It was found that the acetic anhydride had been formed at a rate of 4.6g Ac2 O/g Ni/g I/hour. Patent; Shell Oil Company; US4536354; (1985); (A1) English View in Reaxys 1.c : c. c. 4,6-Dimethyl-5-heptene-2-one according to Helv. Chim. Acta 30, 2216 (1947). The bromide (274 g.), obtained according to paragraph (b) hereinabove, was added at a temperature comprised between -5° and -10° to acetylacetate (obtained from 40.7 g. of sodium and 230 g. of ethyl acetylacetate) in 670 ml. of anhydrous ethanol. The reaction mixture was allowed to react during 2 days at 20° and, after the usual treatments of extraction and drying, 252 g. of the ketoester intermediate were obtained. Patent; Firmenich SA; US3931326; (1976); (A1) English View in Reaxys 3.b : b. b. 5,6-Dimethyl-5-hepten-2-one according to Helv. Chim. Acta 23, 964 (1940). The bromide (261 g.), obtained according to paragraph (a) hereinabove, was added at 6°-10° to acetyl acetate (obtained from 38.8 g. of sodium and 219 g. of ethylacetacetate) in 600 ml of anhydrous ethanol. The reaction mixture was allowed to react during one night at 20° and at reflux during 1.5 h. After dilution with 5-fold its volume of water and the usual treatments of extraction and drying, 263 g. (77 percent) of the ketoester intermediate were obtained. The distillation gave also a fraction with B.p. 30°-42°/0.001 Torr, 35 g., and a residue of 0.5 g. Patent; Firmenich SA; US3931326; (1976); (A1) English View in Reaxys 5 : EXAMPLE 5 EXAMPLE 5 2 g phosphorus trichloride and 2 g phosphorus pentachloride were dissolved with 2 g cupric chloride in 500 ml glacial acetic acid and 50 ml acetic anhydride and then further treated a described in Example 4. 5.2 g propylene glycol diacetate were obtained. Patent; Rohm GmbH; US3981908; (1976); (A1) English View in Reaxys 5 : Preparation of the compound having the formula STR24 EXAMPLE 5 Preparation of the compound having the formula STR24 A partial solution of finely ground potassium permanganate (3.6 gms., 22.8 mmoles) in 25 mls. glacial acetic acid/8 mls. acetic anhydride was prepared in a 3-neck round bottom flask fitted with a mechanical stirrer and thermometer. Patent; Polaroid Corporation; US4107176; (1978); (A1) English View in Reaxys 17.a : 9-Keto-15α-acetoxy-16,16-dimethyl-18-oxa-prosta-2,13-dienic acid EXAMPLE 17a 9-Keto-15α-acetoxy-16,16-dimethyl-18-oxa-prosta-2,13-dienic acid 128.5 mg 9-keto-15α-hydroxy-16,16-dimethyl-18-oxa-prosta-2,13-dienic acid were dissolved in 1 ml of absolute pyridine, and this solution was added to a mixture of 1 ml of pyridine and 1 ml of acetic anhydride prepared at 0° C. Patent; Hoechst Aktiengesellschaft; US4182773; (1980); (A1) English View in Reaxys

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1 : EXAMPLE 1 STR7 Analysis for C10 H7 NO2 (molecular weight 173.17): calculated: C, 69.36percent; H, 4.08percent; N, 8.09percent; found: C, 69.37percent; H, 4.24percent; N, 8.04percent. The acetic anhydride recovered when the solution is concentrated can be re-used after distillation. Patent; Ciba-Geigy Corporation; US4179444; (1979); (A1) English View in Reaxys 2 : EXAMPLE 2 Recrystallization from 300 milliliters of a 4:1 mixture of acetic acid and acetic anhydride yielded 171.3 grams of pure 1,2-bis(4-acetoxyphenyl)ethane, melting point 115°-116° C. Patent; Monsanto Company; US4156787; (1979); (A1) English View in Reaxys 3.b : (b) (b) Preparation of penta-N-protected derivative (IV) 6'-N-Benzyloxycarbonyl-3',4'-dideoxykanamycin B (1.59 g.; 2.72 milimole) was admixed with 160 ml. of acetic anhydride and 16 g. of sodium acetate, and the admixture so obtained was heated for 2 hours under reflux (at 110° C.) to effect the acetylation. The reaction mixture was concentrated to dryness under reduced pressure, and the solid residue was extracted with about 100 ml. of acetone. Patent; Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai; US4120955; (1978); (A1) English View in Reaxys 3 : Preparation of 2-Phenyl-3-benzoyl-6-methoxybenzothiophene A mixture of 53 g. (0.153 mole) of the above phenylacetic acid and 63 g. (0.765 mole) of anhydrous sodium acetate in 780 g. (7.65 mole) of acetic anhydride was prepared. The mixture was stirred, heated slowly to reflux, and maintained at reflux for 15 minutes. The excess acetic anhydride then was hydrolyzed by careful dropwise addition of 1 l. of water. The resulting mixture was poured over ice and diluted to 3.5 l. by addition of ice. A brown precipitate formed and was collected and washed well with cold water. Patent; Eli Lilly and Company; US4133814; (1979); (A1) English View in Reaxys 4.12 : N.M.R. (12) Starting from a mixture of 2-ethoxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3carboxylate (900 mg), hydroxylamine hydrochloride (167 mg) and sodium acetate (341 mg) in acetic acid (7 ml) and acetic anhydride (1 ml) was obtained by applying an essentially similar manner to that of Example 4-2), crystals (420 mg) of 2-ethoxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-cyano-1,4-dihydropyridine-3-carboxylate, m.p. 129° to 130.5° C. (recrystallized from a mixture of diethyl ether and n-hexane). Patent; Fujisawa Pharmaceutical Co., Ltd.; US4145432; (1979); (A1) English View in Reaxys 6.b : Synthesis of 3',4'-dideoxykanamycin C (b) 6'-N-Benzyloxycarbonyl-3',4'-dideoxykanamycin B (1.59 g; 2.72 millimole) was admixed with 160 ml of acetic anhydride and 16 g of sodium acetate, and the admixture so obtained was heated for 2 hours under reflux (at 110° C.) to effect the acetylation. The reaction mixture was concentrated to dryness under reduced pressure, and the solid residue was extracted with about 100 ml of acetone. Patent; Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai; US4140849; (1979); (A1) English View in Reaxys Acetic anhydride(50 equivalents) Acetic anhydride(50 equivalents) TEA (2 equivalents) in CH2 Cl2 (20 ml.): Stir for 2 hours.

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Patent; Imperial Chemical Industries Limited; US4123523; (1978); (A1) English View in Reaxys 2 : CONTROL B--REPLACEMENT OF ACETIC ANHYDRIDE BY ACETIC ACID CONTROL B--REPLACEMENT OF ACETIC ANHYDRIDE BY ACETIC ACID Using the procedure of Example 2, the reaction flask was charged with 17.3 grams (92 millimoles) of 81percent cumene hydroperoxide, 15.2 grams (108 millimoles) of 2-phenyl-2-propanol, and 84 ml of glacial acetic acid. Then 4 ml the perchloric acid catalyst solution described in Example 1 was added dropwise over a period of 5 minutes holding the reaction temperature at 17°+-1° C. After 131 minutes, 16.5percent of the hydroperoxide remained unreacted and after a total of 245 minutes 8.0percent hydroperoxide remained unreacted. The reaction mixture was warmed to 23°+-2° C., neutralized with excess sodium acetate, and worked up essentially as in Example 2 to afford 24.6 grams of crude product. Patent; Union Carbide Corporation; US4198528; (1980); (A1) English View in Reaxys 10 : EXAMPLE 10 EXAMPLE 10 Into a 300 ml rocker bomb was charged: Toluene 50 ml Acetic Anhydride 11.4 ml Sulfuric Acid 0.11 g The bomb was pressurized with 30 psi oxygen and 145 psi nitrogen, i.e. total of 175 psi at room temperature. The reactor was heated at 130° for an 8 hour period; no pressure drop was observed and no oxidation products were detected in the reaction mixture at the end of the reaction. Patent; Suntech, Inc.; US4237310; (1980); (A1) English View in Reaxys c : c) c) With acetic acid anhydride. 0.5 Mol of 2,5-dimethyl-3-thiaadipic acid, 300 ml of acetic acid anhydride and 4g LiCl is stirred for 6 hours at 120°. The crude mixture is poured onto ice, and 10 cm3 H2SO4 conc. are added thereto. The mixture is then stirred overnight, rendered alkaline with conc. NaOH solution, while cooling with pieces of ice, and extracted several times with diethylether. The ether phase is washed with water, dried over MgSO4 and concentrated by evaporation. The residue is distilled over a Vigreux column to give the title compound b.p. 81-88° at 20 Torr. Patent; SANDOZ AG; SANDOZ-PATENT-GMBH; SANDOZ-ERFINDUNGEN Verwaltungsgesellschaft m.b.H.; EP210320; (1987); (A1) English View in Reaxys 33 : Example 33 Example 33 This Example was carried out as described in Example 31, except that LiI was not added and, instead, zirconyl diacetate (200 molpercent to rhodium) and a tetraammonium salt, i.e., tetraethylammonium iodide(2000 molpercent to rhodium) were added as promoters; and the reaction was conducted at 165°C and 800 psi for 2 hrs. The yield of acetic anhydride was about 90percent. Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; EP636599; (1995); (A1) English View in Reaxys C.B : Comparative Example B Comparative Example B Acetylation of CMI DS 1. 0 with NaOAc and acetic anhydride at 120 °C A suspension of CMI (10 g, DS 1.0) and sodium acetate (0.5 g) in acetic anhydride (50 ml) was heated (120°C, 4 hours). After cooling to room temperature the precipitate was removed by means of filtration and the residue was washed with acetic anhydride. The filtrate was concentrated under vacuum (Rotavapor).

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The residue was then taken up in water and freeze-dried. Yield: 7.7 g (68percent). DSacetyl: 0.78. Reaction efficiency: 7percent. Patent; Cooeperatie Cosun U.A.; EP1190034; (2004); (B1) English View in Reaxys 2 : Preparation of Erythromycin A 9-oxime 9,2',4"-triacetate (Compound of formula (I-c)). Example 2 Preparation of Erythromycin A 9-oxime 9,2',4"-triacetate (Compound of formula (I-c)). To a solution of erythromycin A oxime (1.0 kg) in EtOAc (4 L, 4 volumes) was added TEA (0.744 L) and DMAP (48.9 g). While agitating and maintaining a temperature of less than 40° C., to the resulting reaction mixture was added acetic anhydride (0.441 L) over a period of 1-5 hrs. Patent; Xu, Guoyou; Tang, Datong; Gai, Yonghua; Kim, Heejin; Wang, Guoqiang; Phan, Ly Tam; Or, Yat Sun; Wang, Zhe; US2004/171818; (2004); (A1) English View in Reaxys Polymer Synthesis and Characterization Polymer Synthesis and Characterization CPH diacid was synthesised by a method similar to that described previously (Conix, A. (1966) Macromol. Synth. 2, 95-98) for 1,3bis(p-carboxyphenoxy) propane, using p-carboxy benzoic acid (99+percent) and 1,6-dibromohexane (98percent). Diacid was purified by recrystallization three times from N-methyl-2-pyrrolidinone. CPH diacid and SA diacid were acetylated to form the prepolymers by refluxing in excess acetic anhydride for 30 minutes (SA) or 60 minutes (CPH) under dry nitrogen sweep. Patent; Iowa State University Research Foundation, Inc.; US2010/21546; (2010); (A1) English View in Reaxys 31 : Preparation of (3S,4R,5R,6S)-6-(propa-1,2-dienyl)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (60) To the acetonide (compound 59, 2.3 mg, 8.5 mmol) in a round-bottom flask and cooled in an ice-bath was added icecold 10percent H2O/TFA (4 mL) and the mixture was stirred for 1 h. After concentration under reduced pressure, the resulting residue was treated with pyridine (2 mL), DMAP (0.5 mg) and acetic anhydride (2 mL). Patent; Seattle Genetics, Inc.; US8163551; (2012); (B2) English View in Reaxys 31 : Example 31 To the acetonide (compound 59, 2.3 mg, 8.5 mmol) in a round-bottom flask and cooled in an ice-bath was added icecold 10percent H2O/TFA (4 mL) and the mixture was stirred for 1h. After concentration under reduced pressure, the resulting residue was treated with pyridine (2 mL), DMAP (0.5 mg) and acetic anhydride (2 mL). With pyridine, trifluoroacetic acid in water Patent; Seattle Genetics, Inc.; ALLEY, Stephen, C.; JEFFREY, Scott, C.; SUSSMAN, Django; BENJAMIN, Dennis, R.; TOKI, Brian; BURKE, Patrick, J.; EP2282773; (2014); (B1) English View in Reaxys zur Durchfuehrung dieses Verfahrens in der Technik Benson; ; vol. 47; p. 150; ; (1940); p. 3025 View in Reaxys 375 : 1-[3-(acetylamino)propyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide Example 375 1-[3-(acetylamino)propyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide This compound was prepared from 1-(3-aminopropyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide and acetic anhydride employing methods similar to those described in Step 2 of Example 373 and was obtained as a white solid: ES+MS: 485 (M+H+).

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Patent; ViiV Healthcare Company; Shionogi and Co., Ltd.; JOHNS, Brian Alvin; BOROS, Eric Eugene; KAWASUJI, Takashi; KOBLE, Cecilia S.; KUROSE, Noriyuki; MURAI, Hitoshi; SHERRILL, Ronald George; WEATHERHEAD, Jason G.; US2015/225399; (2015); (A1) English View in Reaxys 5 : Example 5 Example 5 A colorless transparent film formed from a polymer compound (resin) containing a repeating unit represented by the following Formula (23) was obtained in the same manner as in Example 1 described above, except that 2,6-pyridinedicarboxyaldehyde was used instead of isophthalaldehyde. The results of measuring the refractive index (nD 25) of the film thus obtained are presented in Table 2. Furthermore, the results for NMR are described below. The acylhydrazone bond equivalent of the compound thus obtained was 246.81. 1H-NMR (270 MHz, d6-DMSO): δ ppm=11.82 (br, 2H), 8.21, 7.92 (br, 2H), 8.06-7.65 (m, 3H), 7.34 (br, 4H), 7.13 (br, 4H), 4.11, 3.89 (br, 4H). Patent; MITSUI CHEMICALS, INC.; Fujii, Shunsuke; Maekawa, Shintaro; Onishi, Hitoshi; Kagayama, Akifumi; (37 pag.); US9221949; (2015); (B2) English View in Reaxys O

Rx-ID: 39090137 View in Reaxys 2/501 Yield

Conditions & References

92 %Spectr.

With gallium trifluoromethanesulfonate, Time= 6h, T= 100 °C Liang, Shengzong; Hammond, Gerald B.; Xu, Bo; Chemical Communications; vol. 51; nb. 5; (2015); p. 903 - 906 View in Reaxys

O O

Rx-ID: 40562103 View in Reaxys 3/501 Yield

Conditions & References With diisopropyl-carbodiimide in toluene, Time= 2h, T= 20 °C Hofmann, Christine; Schümann, Jan M.; Schreiner, Peter R.; Journal of Organic Chemistry; vol. 80; nb. 3; (2015); p. 1972 - 1978 View in Reaxys N

Rx-ID: 23857907 View in Reaxys 4/501 Yield

Conditions & References 49 : N-(8-Bromoquinolin-3-yl)-1,2,3,4-tetrahydro-N-acetyl-7-isoquinolinesulfonamide Example 49 N-(8-Bromoquinolin-3-yl)-1,2,3,4-tetrahydro-N-acetyl-7-isoquinolinesulfonamide White crystals (180 mg) were obtained in the same manner as in Example 1, except using 145 mg (0.65 mmol) of 3amino-8-bromoquinoline (Preparation Example 5) and 277 mg (0.85 mmol) of 1,2,3,4-tetrahydro-2-(trifluoroacetyl)isoquinoline-7-sulfonyl chloride. To the crystals were added ethanol (20 ml) and 1 N sodium hydroxide aqueous solution (0.5 ml), followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 1 N hydrochloric acid (0.4 ml), followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. To the resulting residue were added pyridine (0.5 ml) and acetic anhydride (0.014 ml), followed by stirring at room temperature for 1 hour.

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Patent; Haneda, Toru; Tsuruoka, Akihiko; Kamata, Junichi; Okabe, Tadashi; Takahashi, Keiko; Nara, Kazumasa; Hamaoka, Shinichi; Ueda, Norihiro; Wakabayashi, Toshiaki; Funahashi, Yasuhiro; Semba, Taro; Hata, Naoko; Yamamoto, Yuji; Ozawa, Yoichi; Tsukahara, Naoko; Owa, Takashi; US2003/144507; (2003); (A1) English View in Reaxys 48.iii : 48(iii) 48(iii) Ethyl 2-acetoxymethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate Following a procedure similar to that described in Preparation 44(iii), 1.54 g of diethyl 2-acetoxymethylimidazole-4,5dicarboxylate were reacted with 6.5 equivalents of methylmagnesium iodide. Ethyl acetate was then added to the reaction solution, whilst ice-cooling, and the reaction solution was concentrated by evaporation under reduced pressure. The resulting residue was mixed with 50 ml of pyridine and 25 ml of acetic anhydride, and left at room temperature overnight. At the end of this time, 10 ml of methanol were added to the reaction solution, which was then stirred for 30 minutes. Patent; Sankyo Company, Limited; US5616599; (1997); (A1) English View in Reaxys 7.iii : 7(iii) 7(iii) Ethyl 2-acetoxymethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate Following a procedure similar to that described in Preparation 3(iii), 1.54 g of diethyl 2-acetoxymethylimidazole-4,5dicarboxylate were reacted with 6.5 equivalents of methylmagnesium iodide. Ethyl acetate was then added to the reaction solution, whilst ice-cooling, and the reaction solution was concentrated by evaporation under reduced pressure. The resulting residue was mixed with 50 ml of pyridine and 25 ml of acetic anhydride, and left at room temperature overnight. At the end of this time, 10 ml of methanol were added to the reaction solution, which was then stirred for 30 minutes. Patent; SANKYO COMPANY LIMITED; EP573218; (1993); (A2) English View in Reaxys A.1.e : Preparation of Compound No. 64 (e) 9.1 g (10.7 mmol) of disaccharide No. (62) are dissolved in 100 ml of methylene chloride, and the solution is treated, at RT, with 5 ml of a 90percent trifluoroacetic acid. After approx. 6 h, the mixture is neutralized with a saturated solution of sodium hydrogen carbonate, diluted with ethyl acetate and extracted successively with water and a saturated solution of sodium chloride. The organic phase is dried over sodium sulfate and concentrated by evaporation. The resulting residue is treated with 7 ml of pyridine and 3.5 ml of acetic anhydride, and stirred at RT overnight. Patent; GlycoTech Corp.; US6187754; (2001); (B1) English View in Reaxys 34 : Preparation of (2S,4R,5R,6S)-3,3-difluoro-6-methyl-tetrahydro-2H-pyran-2,4,5-triyl triacetate (65) and (2R, 4R,5R,6S)-3,3-difluoro-6-methyl-tetrahydro-2H-pyran-2,4,5-triyl triacetate (66) 2-deoxy-2,2-difluorofucopyranose-1,3,4-triacetate (65 and 66): To a mixture of the fluorofucal (64, 50 mg, 0.216 mmol) in DMF/H2O (1 mL, 1:1 mixture) was added Selectfluor.(R). and the reaction mixture was stirred overnight at an ambient temperature. The reaction mixture was poured into EtOAc (100 mL) and washed with water (3*50 mL) and brine, dried over NaSO4, decanted and concentrated. The resulting residue was acetylated with a mixture of pyridine (1 mL), DMAP (2 mg) and acetic anhydride (1 mL). Patent; Seattle Genetics, Inc.; US8163551; (2012); (B2) English View in Reaxys 34 : Example 34 2-deoxy-2,2-difluorofucopyranose-1,3,4-triacetate (65 and 66): To a mixture of the fluorofucal (64, 50 mg, 0.216 mmol) in DMF/H2O (1 mL, 1:1 mixture) was added Selectfluor® and the reaction mixture was stirred overnight at an ambient temperature.

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The reaction mixture was poured into EtOAc (100 mL) and washed with water (3 x 50 mL) and brine, dried over NaSO4, decanted and concentrated. The resulting residue was acetylated with a mixture of pyridine (1 mL), DMAP (2 mg) and acetic anhydride (1 mL). in water, DMFA Patent; Seattle Genetics, Inc.; ALLEY, Stephen, C.; JEFFREY, Scott, C.; SUSSMAN, Django; BENJAMIN, Dennis, R.; TOKI, Brian; BURKE, Patrick, J.; EP2282773; (2014); (B1) English View in Reaxys O

O C

Rx-ID: 38740002 View in Reaxys 5/501 Yield

Conditions & References 4 : Example 4 A liquid reaction composition comprising methyl acetate, acetic acid, methyl iodide, acetic anhydride, Group VIII metal catalyst, catalyst promoter and optionally lithium iodide was continuously fed to a commercial scale reactor. Carbon monoxide gas contacted the reaction composition in the reactor by means of a sparging device to produce acetic anhydride and acetic acid. The liquid reaction mixture was continuously withdrawn from the reactor and passed via a flashing valve to a flash zone operated at a reduced pressure compared to the reactor to form an overhead vapour fraction comprising acetic acid and acetic anhydride and a liquid fraction comprising acetic acid and the catalyst components. The amounts of acetic acid, acetic anhydride produced (tpd (tonnes per day)) in the presence and absence of the metal salt are shown in Table 2. Table 2 The results of Table 2 clearly demonstrate that the present invention provides for an increased production rate of acetic anhydride relative to acetic acid without necessitating an increase in the concentration of acetic anhydride in the reactor. With lithium iodide, methyl iodide, Large scale, Reagent/catalyst Patent; BP CHEMICALS LIMITED; HENNIGAN, Sean, Anthony; WO2014/135664; (2014); (A2) English View in Reaxys

OH OH O

O NH 2 Cl OH

HO H

NH 2

Z O

HO OH

Rx-ID: 39219664 View in Reaxys 6/501 Yield

Conditions & References 2.2. Electrochemical system Volumes of 0.1 L of each pharmaceutical solution were introduced into a single compartment electrolytic cell with constant stirring at 25°C. A BDD thin film (on Si) electrode from Adamant Technologies was used as anode andan AISI 304 stainless steel plate as cathode, both 5 cm2 geometric area, with 1.0 cm of interelectrode gap. Solutions of each drug containing 100 mg L-1 of total organic carbon were prepared in 0.1 M Na2SO4 to provide enough ionic strength at pH 7.0 were treated by EO at a current density (j) of 50 mA cm-2,resulting in average cell voltages of 13.0 (±0.3) V. With water, sodium sulfate, pH= 7, Electrochemical reaction Espinoza, C.; Contreras, N.; Berros, C.; Salazar, R.; Journal of the Chilean Chemical Society; vol. 59; nb. 2; (2014); p. 2507 - 2511 View in Reaxys

O O

Rx-ID: 35440688 View in Reaxys 7/501 Yield

Conditions & References 1 : Synthesis of diketene

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The bubbler and three glass cylinder traps were charged with 300 ml of dry acetone (99.5percent) each and the traps were immersed in a dry ice/acetone bath at a temperature of minus 72 °C. The fourth glass trap was charged with 150 ml of acetone at room temperature. The condenser was connected to circulating cold water (8 - 12 °C) from a separate water/ice bath. The furnace temperature was set to 620 °C and argon was passed through the bubbler with acetone at a flow rate 0.7 - 1.0 1/min to deliver acetone vapour to the quartz tube reactor. Temperature of acetone in the bubbler was maintained by a water bath at about 40 °C. The furnace temperature was kept at range of 620 - 670 °C to maintain temperature of the silica foam disk in the reactor at 470 - 510 °C. After 4 hours of the continuous passing of acetone stream vapour through the quartz reactor the furnace was turned off and the argon flow was reduced to 0.1 1 min. When the quartz tube reached room temperature the argon flow was stopped and the reactor system including three glass cylinder traps immersed in a dry ice/acetone bath was left to stand overnight. The acetone solutions from the three traps were collected and the solvent was evaporated under vacuum at a temperature range of 25 - 30 °C. The resulting dark red concentrate was distilled under vacuum at 55 - 70 °C using a cold finger (cooled with acetone/dry ice) and the formed white solid was melted into a separate flask to give a yellowish liquid weighing 16.5 g, including 75percent of diketene, 16percent of acetic anhydride and 5percent of acetic acid. The diketene was taken forward into the next step without further purification. With hydrogen, Time= 4h, T= -72 - 510 °C , Inert atmosphere, Sealed tube Patent; PIONEER ENERGY; HENRI, John; ZYGMUNT, Jan; BERGREN, Mark; ZUBRIN, Robert; WO2013/70966; (2013); (A1) English View in Reaxys O

O C

Rx-ID: 5263767 View in Reaxys 8/501 Yield

Conditions & References With methyl iodide, Rhodium trichloride, triphenylphosphine, T= 190 °C , p= 37503Torr , Carbonylation, Kinetics, Further Variations: Catalysts Terekkova; Kolesnichenko; Batov; Alieva; Trukhmanova; Slivinskii; Pesin; Plate; Russian Chemical Bulletin; vol. 48; nb. 4; (1999); p. 818 - 819 View in Reaxys With hydrogen, chitosan, methyl iodide, Rhodium trichloride in acetic acid, T= 190 °C , p= 37503Torr , Kinetics, Further Variations: Reagents Kolesnichenko, N. V.; Batov, A. E.; Markova, N. A.; Slivinsky, E. V.; Russian Chemical Bulletin; vol. 51; nb. 2; (2002); p. 259 - 262; Izvestiya Akademi Nauk, Seriya Khimicheskaya; nb. 2; (2002); p. 246 - 249 View in Reaxys 1; 2 :Comparative Example 1In this comparative example, a batch process without adding the promoter of the present invention was used, as a comparative experiment, to carry out the carbonylation reaction. The following constituents with specified amounts were fed into the reactor: 50 wt. percent of methyl acetate, 25 wt. percent of methyl iodide, 5 wt. percent of acetic anhydride, lithium iodide (40000 ppm of Li ion), 800 ppm of the Rh catalyst, and an appropriately balanced amount of acetic acid as a solvent. The reactor into which the mixture of the aforementioned reactants had been fed was firstly pressurized with hydrogen to 1 kg/cm2, and then carbon monoxide was introduced into the reactor, followed by a gradual elevation of temperature. After the set temperature for the reaction was reached, carbon monoxide was resupplied so that the inner pressure of the system reached 27 kg/cm2. During the reaction, carbon monoxide kept on being resupplied with the consumption of carbon monoxide so that the pressure stably maintained 27 kg/cm2. The consumption of carbon oxide was recorded and a constituent analysis was carried out by sampling so as to calculate the unit space-time yield (STY) of acetic anhydride (unit: mole/liter*hour).; Examples 1214Influence of Added Amount of Organic Promoters on Reaction RateThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent, wt. percent and 6 wt. percent of organic promoters, N-acetylimidazole, were added in the reaction media. The experimental results were recorded in Table 4. It is obvious from Table 4 that the STY values of the carbonylation reaction were increased synchronously with the increase in the added amount of organic promoter, which shows the carbonylation reaction rate can indeed be satisfactorily increased by the increase in the added amount of these kinds of organic promoters according to the present invention. In addition, when the Example 14 is compared with the Comparative Example 1, it is found that the addition of these kinds of organic promoters can maintain the original reaction rate with the added amount of lithium iodide reduced, which shows these kinds of organic promoters and lithium iodide have the same or even better effect of stabilizing the catalyst. Another advantage is that the used amount of lithium iodide in the process can be reduced so that the load of the deiodination process in the later stage can be reduced. TABLE 4 Influ-

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ence of Added Amount of Organic Promoters on Reaction Rate STY Content of Li+ value Organic Promoter Temp. Pressure (LiI) (gmol/ Reagents (wt percent) (° C.)(kg/cm2) (ppm) L * hr) Compar. 190 27 4000 9.13 Example 1 Example 7 N-acetyl- 2 190 27 4000 10.78 Example imidazole 4 190 27 4000 11.33 12 Example 6 190 27 4000 12.06 13 Compar. 190 27 3000 8.22 Example 2 Example N-acetyl- 4 190 27 3000 10.96 14 imidazole With hydrogen, lithium iodide, methyl iodide, rhodium in acetic acid, T= 190 °C , p= 19860.5Torr , Product distribution / selectivity Patent; China Petrochemical Development Corporation; US7553991; (2009); (B1) English View in Reaxys 3 :Examples 17Improved Performance on Reaction Rate of Acetic Anhydride (STY) by Addition of Different Organic PromotersThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoters were added in the reaction media. The results of the Examples 17 and the Comparative Example 1 were recorded in Table 1, and the Comparative Example 1 was a blank experiment that no organic promoter was added. It is obvious from Table 1 that the STY values for those having the organic promoters added were all increased by 6percent20percent, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate. TABLE 1 Influence of Addition of Organic Promoters on Reaction Rate Temp. Content of Organic Promoter (° C.)/ (wt Pressure STY value Reagents percent)(kg/cm2) (gmol/L * hr) Compar. 190/27 9.13 Example 1 Example 1 4-pyrrolidionpyridine 2 190/27 9.68 Example 2 5-amino-3-methyl-1- 2 190/27 9.87 phenylpyrazole Example 3 3-acetoxypyridine 2 190/27 10.05 Example 4 2-methylbenzimidazole 2 190/27 10.42 Example 5 5-amino-1,3- 2 190/27 10.60 dimethylpyrazole Example 6 N-methylbenzimidazole 2 190/27 10.78 Example 7 N-acetylimidazole 2 190/27 10.78 With pyridin-3-yl acetate, hydrogen, lithium iodide, methyl iodide, rhodium in acetic acid, T= 190 °C , p= 19860.5Torr , Product distribution / selectivity Patent; China Petrochemical Development Corporation; US7553991; (2009); (B1) English View in Reaxys 5; 8; 9 :Examples 17Improved Performance on Reaction Rate of Acetic Anhydride (STY) by Addition of Different Organic PromotersThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoters were added in the reaction media. The results of the Examples 17 and the Comparative Example 1 were recorded in Table 1, and the Comparative Example 1 was a blank experiment that no organic promoter was added. It is obvious from Table 1 that the STY values for those having the organic promoters added were all increased by 6percent20percent, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate. TABLE 1 Influence of Addition of Organic Promoters on Reaction Rate Temp. Content of Organic Promoter (° C.)/ (wt Pressure STY value Reagents percent)(kg/cm2) (gmol/L * hr) Compar. 190/27 9.13 Example 1 Example 1 4-pyrrolidionpyridine 2 190/27 9.68 Example 2 5-amino-3-methyl-1- 2 190/27 9.87 phenylpyrazole Example 3 3-acetoxypyridine 2 190/27 10.05 Example 4 2-methylbenzimidazole 2 190/27 10.42 Example 5 5-amino-1,3- 2 190/27 10.60 dimethylpyrazole Example 6 N-methylbenzimidazole 2 190/27 10.78 Example 7 N-acetylimidazole 2 190/27 10.78.; Examples 89Influence of Reaction Pressure and Organic Promoters on Reaction RateThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoter, 5-amino-1,3-dimethylpyrazole, was added in the reaction media and the CO pressure was altered. The experimental results were recorded in Table 2. It is obvious from Table 2 that the STY values of the carbonylation reaction for those having the organic promoter added and the CO pressure increased could be increased. In other words, the increase in the reaction pressure can increase the reaction rate, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate at different reaction pressures. TABLE 2 Influence of Reaction Pressure and Organic Promoters on Reaction Rate STY Content of Li+ value Organic Promoter Temp. Pressure (LiI) (gmol/ Reagents (wt percent) (° C.)(kg/cm2) (ppm) L * hr) Com- 190 27 4000 9.13 par. Exam- ple 1 Exam- 5-amino-1,3- 2 190 27 4000 10.60 ple 2 dimethyl- Exam- pyrazole 2 190 32 4000 11.15 ple 8 Exam- 2 190 40 4000 11.69 ple 9 With N-(2,5-dimethyl-2H-pyrazol-3-yl)-amine, hydrogen, lithium iodide, methyl iodide, rhodium in acetic acid, T= 190 °C , p= 19860.5 - 29422.9Torr , Product distribution / selectivity Patent; China Petrochemical Development Corporation; US7553991; (2009); (B1) English View in Reaxys 2 :Examples 17Improved Performance on Reaction Rate of Acetic Anhydride (STY) by Addition of Different Organic PromotersThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoters were added in the reaction media. The results of the Examples 17

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and the Comparative Example 1 were recorded in Table 1, and the Comparative Example 1 was a blank experiment that no organic promoter was added. It is obvious from Table 1 that the STY values for those having the organic promoters added were all increased by 6percent20percent, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate. TABLE 1 Influence of Addition of Organic Promoters on Reaction Rate Temp. Content of Organic Promoter (° C.)/ (wt Pressure STY value Reagents percent)(kg/cm2) (gmol/L * hr) Compar. 190/27 9.13 Example 1 Example 1 4-pyrrolidionpyridine 2 190/27 9.68 Example 2 5-amino-3-methyl-1- 2 190/27 9.87 phenylpyrazole Example 3 3-acetoxypyridine 2 190/27 10.05 Example 4 2-methylbenzimidazole 2 190/27 10.42 Example 5 5-amino-1,3- 2 190/27 10.60 dimethylpyrazole Example 6 N-methylbenzimidazole 2 190/27 10.78 Example 7 N-acetylimidazole 2 190/27 10.78 With 5-amino-3-methyl-1-phenyl-(1H)-pyrazole, hydrogen, lithium iodide, methyl iodide, rhodium in acetic acid, T= 190 °C , p= 19860.5Torr , Product distribution / selectivity Patent; China Petrochemical Development Corporation; US7553991; (2009); (B1) English View in Reaxys 7; 12; 13; 14 :Examples 17Improved Performance on Reaction Rate of Acetic Anhydride (STY) by Addition of Different Organic PromotersThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoters were added in the reaction media. The results of the Examples 17 and the Comparative Example 1 were recorded in Table 1, and the Comparative Example 1 was a blank experiment that no organic promoter was added. It is obvious from Table 1 that the STY values for those having the organic promoters added were all increased by 6percent20percent, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate. TABLE 1 Influence of Addition of Organic Promoters on Reaction Rate Temp. Content of Organic Promoter (° C.)/ (wt Pressure STY value Reagents percent)(kg/cm2) (gmol/L * hr) Compar. 190/27 9.13 Example 1 Example 1 4pyrrolidionpyridine 2 190/27 9.68 Example 2 5-amino-3-methyl-1- 2 190/27 9.87 phenylpyrazole Example 3 3-acetoxypyridine 2 190/27 10.05 Example 4 2-methylbenzimidazole 2 190/27 10.42 Example 5 5-amino-1,3- 2 190/27 10.60 dimethylpyrazole Example 6 N-methylbenzimidazole 2 190/27 10.78 Example 7 N-acetylimidazole 2 190/27 10.78.; Examples 1214Influence of Added Amount of Organic Promoters on Reaction RateThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent, wt. percent and 6 wt. percent of organic promoters, N-acetylimidazole, were added in the reaction media. The experimental results were recorded in Table 4. It is obvious from Table 4 that the STY values of the carbonylation reaction were increased synchronously with the increase in the added amount of organic promoter, which shows the carbonylation reaction rate can indeed be satisfactorily increased by the increase in the added amount of these kinds of organic promoters according to the present invention. In addition, when the Example 14 is compared with the Comparative Example 1, it is found that the addition of these kinds of organic promoters can maintain the original reaction rate with the added amount of lithium iodide reduced, which shows these kinds of organic promoters and lithium iodide have the same or even better effect of stabilizing the catalyst. Another advantage is that the used amount of lithium iodide in the process can be reduced so that the load of the deiodination process in the later stage can be reduced. TABLE 4 Influence of Added Amount of Organic Promoters on Reaction Rate STY Content of Li+ value Organic Promoter Temp. Pressure (LiI) (gmol/ Reagents (wt percent) (° C.)(kg/cm2) (ppm) L * hr) Compar. 190 27 4000 9.13 Example 1 Example 7 N-acetyl- 2 190 27 4000 10.78 Example imidazole 4 190 27 4000 11.33 12 Example 6 190 27 4000 12.06 13 Compar. 190 27 3000 8.22 Example 2 Example N-acetyl- 4 190 27 3000 10.96 14 imidazole With 1-acetyl-1H-imidazole, hydrogen, lithium iodide, methyl iodide, rhodium in acetic acid, T= 190 °C , p= 19860.5Torr , Product distribution / selectivity Patent; China Petrochemical Development Corporation; US7553991; (2009); (B1) English View in Reaxys 4; 10; 11 :Examples 17Improved Performance on Reaction Rate of Acetic Anhydride (STY) by Addition of Different Organic PromotersThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoters were added in the reaction media. The results of the Examples 17 and the Comparative Example 1 were recorded in Table 1, and the Comparative Example 1 was a blank experiment that no organic promoter was added. It is obvious from Table 1 that the STY values for those having the organic promoters added were all increased by 6percent20percent, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate. TABLE 1 Influence of Addition of Organic Promoters on Reaction Rate Temp. Content of Organic Promoter (° C.)/ (wt Pressure STY value Reagents percent)(kg/cm2) (gmol/L * hr) Compar. 190/27 9.13 Example 1 Example 1 4pyrrolidionpyridine 2 190/27 9.68 Example 2 5-amino-3-methyl-1- 2 190/27 9.87 phenylpyrazole Example 3 3-acetoxypyridine 2 190/27 10.05 Example 4 2-methylbenzimidazole 2 190/27 10.42 Example 5 5-amino-1,3- 2 190/27 10.60 dimethylpyrazole Example 6 N-methylbenzimidazole 2 190/27 10.78 Example 7 N-acetylimidazole 2 190/27 10.78.;

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Examples 1011Influence of Reaction Temperature and Organic Promoters on Reaction RateThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoter, 2-methylbenzimidazole, was added in the reaction media and the reaction temperature was altered. The experimental results were recorded in Table 3. It is obvious from Table 3 that the STY values of the carbonylation reaction could still be increased by adding the organic promoter and altering the reaction temperature, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate at different reaction temperatures. In addition, when the Example 11 is compared with the Comparative Example 1, it is found that the addition of these kinds of organic promoters can maintain the original reaction rate at a lower reaction temperature, which has the effect of saving energy and reducing production cost. TABLE 3 Influence of Reaction Temperature and Organic Promoters on Reaction Rate STY Content of Li+ value Organic Promoter Temp. Pressure (LiI) (gmol/ Reagents (wt percent) (° C.)(kg/cm2) (ppm) L * hr) Compar. 190 27 4000 9.13 Example 1 Example 4 2-methyl- 2 190 27 4000 10.42 Example benzimid- 2 200 27 4000 11.33 10 azole Example 4 180 27 4000 9.87 11 With 2-methyl-1H-benzimidazole, hydrogen, lithium iodide, methyl iodide, rhodium in acetic acid, T= 180 - 200 °C , p= 19860.5Torr , Product distribution / selectivity Patent; China Petrochemical Development Corporation; US7553991; (2009); (B1) English View in Reaxys 6 :Examples 17Improved Performance on Reaction Rate of Acetic Anhydride (STY) by Addition of Different Organic PromotersThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoters were added in the reaction media. The results of the Examples 17 and the Comparative Example 1 were recorded in Table 1, and the Comparative Example 1 was a blank experiment that no organic promoter was added. It is obvious from Table 1 that the STY values for those having the organic promoters added were all increased by 6percent20percent, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate. TABLE 1 Influence of Addition of Organic Promoters on Reaction Rate Temp. Content of Organic Promoter (° C.)/ (wt Pressure STY value Reagents percent)(kg/cm2) (gmol/L * hr) Compar. 190/27 9.13 Example 1 Example 1 4-pyrrolidionpyridine 2 190/27 9.68 Example 2 5-amino-3-methyl-1- 2 190/27 9.87 phenylpyrazole Example 3 3-acetoxypyridine 2 190/27 10.05 Example 4 2-methylbenzimidazole 2 190/27 10.42 Example 5 5-amino-1,3- 2 190/27 10.60 dimethylpyrazole Example 6 N-methylbenzimidazole 2 190/27 10.78 Example 7 N-acetylimidazole 2 190/27 10.78 With 1-methyl-benzimidazole, hydrogen, lithium iodide, methyl iodide, rhodium in acetic acid, T= 190 °C , p= 19860.5Torr , Product distribution / selectivity Patent; China Petrochemical Development Corporation; US7553991; (2009); (B1) English View in Reaxys 1 :Examples 17Improved Performance on Reaction Rate of Acetic Anhydride (STY) by Addition of Different Organic PromotersThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 2 wt. percent of organic promoters were added in the reaction media. The results of the Examples 17 and the Comparative Example 1 were recorded in Table 1, and the Comparative Example 1 was a blank experiment that no organic promoter was added. It is obvious from Table 1 that the STY values for those having the organic promoters added were all increased by 6percent20percent, which shows the addition of these kinds of organic promoters according to the present invention indeed has the effect of increasing the carbonylation reaction rate. TABLE 1 Influence of Addition of Organic Promoters on Reaction Rate Temp. Content of Organic Promoter (° C.)/ (wt Pressure STY value Reagents percent)(kg/cm2) (gmol/L * hr) Compar. 190/27 9.13 Example 1 Example 1 4-pyrrolidionpyridine 2 190/27 9.68 Example 2 5-amino-3-methyl-1- 2 190/27 9.87 phenylpyrazole Example 3 3-acetoxypyridine 2 190/27 10.05 Example 4 2-methylbenzimidazole 2 190/27 10.42 Example 5 5-amino-1,3- 2 190/27 10.60 dimethylpyrazole Example 6 N-methylbenzimidazole 2 190/27 10.78 Example 7 N-acetylimidazole 2 190/27 10.78 With hydrogen, 4-pyrrolidin-1-ylpyridine, lithium iodide, methyl iodide, rhodium in acetic acid, T= 190 °C , p= 19860.5Torr , Product distribution / selectivity Patent; China Petrochemical Development Corporation; US7553991; (2009); (B1) English View in Reaxys 13 :Examples 10-13; Influence of Reaction Temperature and Organic Promoter on Reaction RateThe carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 3 wt. percent of the EDA organic promoter was added in the initial reaction media and the reaction temperature was changed. The results were recorded in Table 2. It is obvious from Table 2 that the STY values of the carbonylation reaction can still be increased by adding the organic promoter and changing the reaction temperature, which shows the addition of

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such kind of organic promoter under different reaction temperatures according to the present invention can indeed increase the yield of acetic anhydride. Also, from the comparison between the Examples 10 and 11 and the Comparative Example 1, adding such kind of organic promoter can have a better reaction rate at a lowered reaction temperature, which is energy-saving and can lower the production cost. With hydrogen, methyl iodide, Ethylidene diacetate, lithium iodide in acetic acid, T= 200 °C , p= 735.572 19860.5Torr , Product distribution / selectivity Patent; Wang, Hui Ting; Tsai, Chia Jung; Shen, Chia Hui; US2012/53366; (2012); (A1) English View in Reaxys O

starch acetate Rx-ID: 33665528 View in Reaxys 9/501 Yield

Conditions & References

87%

1 : Preparation of Acetylated Starch by Means of a Method Involving a LIST CRP and Comparison with a Conventional Method 53.33 g, Catalyst: methanesulfonic acid: 0.56 g, Acetic anhydride: 2.83 g, Acetic acid: 95.16 g, Total mass: 151.89 g. The precipitation ratio is 1/10, i.e. 1519 g, and the recovery yield is 87percent. 46.42 g (46.42/53.33*100=87) of dry starch acetate are therefore recovered. Patent; ROQUETTE FRERES; US2012/208897; (2012); (A1) English View in Reaxys

Rx-ID: 34490061 View in Reaxys 10/501 Yield

Conditions & References

1.5 mg, 13.4 mg, 1.4 mg

With 1-phenyl-propane-1,2-dione in methanol, aq. phosphate buffer, Time= 72h, T= 37 °C , pH= 7.4 Nagamatsu, Ryu-Ichiro; Mitsuhashi, Shinya; Shigetomi, Kengo; Ubukata, Makoto; Bioscience, Biotechnology and Biochemistry; vol. 76; nb. 10; (2012); p. 1904 - 1908 View in Reaxys O

Rx-ID: 643186 View in Reaxys 11/501 Yield 90 %

Conditions & References With PEG-1000, sulfated zirconia, Time= 2h, T= 40 °C , neat (no solvent) Hu, Yu Lin; Zhao, Xing E.; Lu, Ming; Bulletin of the Chemical Society of Ethiopia; vol. 25; nb. 2; (2011); p. 255 262 View in Reaxys

88.8 %

With thionyl chloride in dichloromethane, Time= 0.0833333h, T= 22 - 25 °C Fife, Wilmer K.; Zhang, Zhi-dong; Tetrahedron Letters; vol. 27; nb. 41; (1986); p. 4937 - 4940 View in Reaxys durch thermische Zersetzung von Essigsaeure an Katalysatoren, wie z.B.Silicagel oder Al2O3-Gel bei 700-750grad

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Patent; C.F.Boehringer and Soehne; DE566332; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 354 View in Reaxys Patent; C.F.Boehringer and Soehne; US2045718; (1929) View in Reaxys durch thermische Zersetzung von Essigsaeure an Katalysatoren, wie z.B. CuCl2 auf Asbest oder CuCO3 bzw.AgOH auf Bimsstein bei 680-720grad Patent; Berl; FR670659; (1929) View in Reaxys Patent; Berl; US2006787; (1929) View in Reaxys Patent; Berl; CH142149; (1929) View in Reaxys durch thermische Zersetzung von Essigsaeure an Katalysatoren, wie z.B. Calciumwolframat auf Traegersubstanzen bei 550-650grad Patent; Celanese Corp.Am.; US1915572; (1929) View in Reaxys Patent; Celanese Corp.Am.; US2054865; (1929) View in Reaxys Patent; Celanese Corp.Am.; GB314555; (1928) View in Reaxys Patent; Celanese Corp.Am.; GB340484; (1929) View in Reaxys durch thermische Zersetzung von Essigsaeure an Katalysatoren, wie z.B. komplexe Saeuren wie Titanborsaeure,Wolframborsaeure und Silicowolframsaeure bei 740-850grad Patent; C.F.Boehringer and Soehne; DE599630; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 359 View in Reaxys With phosgene, aluminium trichloride Patent; Stickstoffduenger,A.G.; FR669150; (1929) View in Reaxys Patent; Stickstoffduenger,A.G.; DE582318; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 360 View in Reaxys Patent; Stickstoffduenger,A.G.; US1865405; (1931) View in Reaxys With phosgene, magnesium oxide Patent; Stickstoffduenger,A.G.; FR669150; (1929) View in Reaxys Patent; Stickstoffduenger,A.G.; DE582318; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 360 View in Reaxys Patent; Stickstoffduenger,A.G.; US1865405; (1931) View in Reaxys With phosgene, CaO Patent; Stickstoffduenger,A.G.; FR669150; (1929) View in Reaxys Patent; Stickstoffduenger,A.G.; DE582318; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 360 View in Reaxys Patent; Stickstoffduenger,A.G.; US1865405; (1931) View in Reaxys With aluminium trichloride, phosphorus trichoride Patent; Goldschmidt; Wolff; DE594552; (1931); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 367

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View in Reaxys With thionyl chloride Patent; I.G.Farbenind.; US1905466; (1931) View in Reaxys Patent; I.G.Farbenind.; GB354159; (1931) View in Reaxys Patent; I.G.Farbenind.; DE546511; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 267 View in Reaxys With benzene, T= 265 °C , p= 22065.2Torr Patent; Knapsack-Griesheim A.G.; DE951809; (1954) View in Reaxys Patent; Knapsack-Griesheim A.G.; US2872481; (1955) View in Reaxys With pyridine, 2,2,2-trichloroacetyl chloride Gerrard; Thrush; Journal of the Chemical Society; (1952); p. 2117,2119 View in Reaxys With pyridine, dibutylphosphonic acid chloroanhydride, pentane Cade; Gerrard; Journal of the Chemical Society; (1954); p. 2030,2033 View in Reaxys With diethyl ether, methoxy acetylene Eglinton et al.; Journal of the Chemical Society; (1954); p. 1860,1864 View in Reaxys With diethyl ether, ethyl ethynyl ether Arens; Modderman; Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences; vol. 53; (1950); p. 1163,1166 View in Reaxys With platinum, T= 1150 °C Peytral; Bulletin de la Societe Chimique de France; vol. <4> 31; (1922); p. 122 View in Reaxys With pumice stone, T= 650 °C Patent; Konsort.f.elektrochem.Ind.; DE408715; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 259 View in Reaxys With sodium chloride, T= 550 °C Patent; Konsort.f.elektrochem.Ind.; DE408715; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 259 View in Reaxys With titanium oxide, T= 300 °C Compardou; Seon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 186; (1928); p. 592 View in Reaxys With alumina hydrate, phosphoric acid, pumice stone, T= 600 °C Patent; Konsort.f.elektrochem.Ind.; DE410363; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 375 View in Reaxys With alkali phosphate, T= 600 °C , besonders Metaphosphate oder eine Mischung von Alkaliphosphaten, deren Schmelzpunkt unterhalb der Reaktionstemperatur liegt

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Patent; Konsort.f.elektrochem.Ind.; DE417731; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 376 View in Reaxys With phosphorus, T= 680 °C Patent; Konsort.f.elektrochem.Ind.; DE475885; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 631 View in Reaxys With phosphoric acid, T= 680 °C , deren Salzen oder Estern Patent; Konsort.f.elektrochem.Ind.; DE475885; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 631 View in Reaxys With tetrachlorosilane Patent; Konsort.f.elektrochem.Ind.; DE394730; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 255 View in Reaxys With acetyl chloride Patent; Hoechster Farbw.; DE396696; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 254,1484 View in Reaxys Patent; Hoechster Farbw.; DE411519 View in Reaxys With acetyl chloride, T= -20 - -15 °C Patent; Hoechster Farbw.; DE396696; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 254,1484 View in Reaxys Patent; Hoechster Farbw.; DE411519 View in Reaxys With methyleneoxaethylene Patent; Konsort.f.elektrochem.Ind.; DE403863; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 259 View in Reaxys With P2O5 Gal; Etard; Chemische Berichte; vol. 9; (1876); p. 444 View in Reaxys With pyridine, thionyl chloride, diethyl ether Gerrard; Thrush; Journal of the Chemical Society; (1952); p. 741 View in Reaxys With fire-clay, T= 650 °C Patent; Konsort.f.elektrochem.Ind.; DE408715; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 259 View in Reaxys With calcium hydroxide powder, pumice stone, T= 600 °C Patent; Konsort.f.elektrochem.Ind.; DE410363; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 375 View in Reaxys Aus dem beu der pyrogenen Dehydratation entstehenden Gemisch aus Acetanhydrid-Dampf und Wasserdampf laesst sich durch Zusatz von Verbindungen, die mit Wasser azeotrope Gemische bilden, und nachfolgende Kondensation Patent; I.G.Farbenind.; DE486953; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 235 View in Reaxys With thionyl chloride, T= -20 - -15 °C Patent; Hoechster Farbw.; DE396696; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 254,1484 View in Reaxys

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Patent; Hoechster Farbw.; DE411519 View in Reaxys With 2,2,4,4,6,6-hexachlorotriazatriphosphorine, triethylamine in dichloromethane, Time= 0.133333h, T= -10 - 0 °C Gregorio, Francesco Di; Marconi, Walter; Caglioti, Luciano; Journal of Organic Chemistry; vol. 46; nb. 22; (1981); p. 4569 - 4570 View in Reaxys T= 650 °C , Leiten ueber Chamotte oder Bimsstein Patent; Konsort. f. elektrochem. Ind.; DE408715; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 259 View in Reaxys T= 550 °C , Leiten ueber Natriumchlorid Patent; Konsort. f. elektrochem. Ind.; DE408715; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 259 View in Reaxys T= 25 °C , Equilibrium constant Colton, Ian J.; Kazlauskas, Romas J.; Journal of Organic Chemistry; vol. 59; nb. 13; (1994); p. 3626 - 3635 View in Reaxys

Rx-ID: 31688999 View in Reaxys 12/501 Yield

Conditions & References With oxygen, nitrogen(II) oxide, chlorine, p= 697.57Torr , Inert atmosphere, Photolysis Andersen, Vibeke F.; Berhanu, Tesfaye A.; Nilsson, Elna J. K.; Jorgensen, Solvejg; Nielsen, Ole John; Wallington, Timothy J.; Johnson, Matthew S.; Journal of Physical Chemistry A; vol. 115; nb. 32; (2011); p. 8906 8919 View in Reaxys

O C

Rx-ID: 29416649 View in Reaxys 13/501 Yield

Conditions & References 15 :Examples 14-15Influence of Added Amount of Ionic Liquids on Reaction Rate; The carbonylation reactions were carried out under the same conditions as the Comparative Example 1, except that 0.07 mole, 0.10 mole and 0.15 mole of the ionic liquid promoters, N-methyl-4-di(methylamino)pyridinium iodide, were added in the reaction media. The experimental results were recorded in Table 4. It is obvious from Table 4 that the STY values of the carbonylation reaction were increased synchronously with the increase in the added amount of the ionic liquid promoter, which shows the carbonylation reaction rate can indeed be increased by the increase in the added amount of these kinds of ionic liquid promoters according to the present invention. With hydrogen, 4-N,N-dimethylamino-1-methyl-pyridinium iodide, lithium iodide, Rh catalyst, p= 19860.5Torr , Heating, Product distribution / selectivity Patent; Tu, Ching Liang; Shen, Chia Hui; Tsai, Chia Jung; Chen, Chi He; US2010/145098; (2010); (A1) English View in Reaxys O O

O O

Rx-ID: 29466863 View in Reaxys 14/501

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Yield

Conditions & References With D072 mesoporous strong acidic cation-exchange resin, T= -15.16 °C , Inert atmosphere, Kinetics, Equilibrium constant, Temperature Wang, Baohe; Zhang, Haojian; Jing, Xin; Zhu, Jing; Catalysis Communications; vol. 11; nb. 8; (2010); p. 753 757 View in Reaxys

Rx-ID: 31238316 View in Reaxys 15/501 Yield

Conditions & References

66 %, 20 %

With chlorine, T= 51.84 °C , p= 730Torr , Irradiation, chamber system Orlando, John J.; Tyndall, Geoffrey S.; International Journal of Chemical Kinetics; vol. 42; nb. 7; (2010); p. 397 413 View in Reaxys

26 %, 61 %

With chlorine, T= -24.16 °C , p= 730Torr , Irradiation, chamber system Orlando, John J.; Tyndall, Geoffrey S.; International Journal of Chemical Kinetics; vol. 42; nb. 7; (2010); p. 397 413 View in Reaxys O

Rx-ID: 28739700 View in Reaxys 16/501 Yield

Conditions & References 15 :To a 300 mL autoclave was added 0.396 g (1.5 mmol) of RhCl3.3H2O, 112.0 g (0.507 mol) of N-methylpyridinium iodide, 30.0 g (0.5 mol) of acetic acid, and 74.0 g (1.0 mol) of methyl acetate. The mixture was heated to 190° C. under 17.2 barg (250 psig) of 5percent hydrogen in carbon monoxide. Upon reaching 190° C., the pressure was adjusted to 51.7 barg (750 psig) using 5percent hydrogen in CO. The temperature and pressure were maintained for 5 hours using 5percent hydrogen in CO as needed to maintain pressure. After 5 hours, the reaction was cooled, vented, and the product transferred to a sample bottle. GC analysis of the product showed that the mixture contained 1.31percent methyl acetate, 19.55percent acetic anhydride, 32.40percent acetic acid, and 1.70percent of ethylidene diacetate (1,1-diacetoxyethane). No methyl iodide was detected in the product by GC analysis. This example demonstrates that the process is applicable to the synthesis of acetic anhydride using methyl acetate as the carbonylation feedstock. With hydrogen, 1-methylpyridinium iodide, rhodium trichloride 3-hydrate in acetic acid, p= 13689.1 - 39547.2Torr , Product distribution / selectivity Patent; EASTMAN CHEMICAL COMPANY; US2009/247783; (2009); (A1) English View in Reaxys O

O NH

Rx-ID: 27757163 View in Reaxys 17/501 Yield 60 %

Conditions & References To 7V-[(5- methoxy-3,4-dihydro-2H-l,4-benzoxazin-3-yl)methyl]acetamide (0.426 g, 1.8 mmol) in anhydrous dichloromethane (35 mL), under nitrogen at -780C, was added IM boron tribromide in dichloromethane (4.5 mL, 4.5 mmol). The reaction was slowly warmed up to room temperature and stirred at room temperature overnight. It was quenched with saturated sodium bicarbonate and extracted with dichloromethane (IX). The aqueous layer was then extracted with ethyl acetate (3X), the ethyl acetate extracts pooled, treated with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. Flash column chromatography on silica gel using (9:1) dichloromethanemethanol afforded 0.241 g (60percent) of desired product as a gum. MS (ES) m/z 223.1 [M+η]+.

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Stage 1: With boron tribromide in dichloromethane, T= -78 - 20 °C Stage 2: With water, sodium hydrogencarbonate in dichloromethane Patent; WYETH; WO2008/52075; (2008); (A2) English View in Reaxys O

Rx-ID: 27967165 View in Reaxys 18/501 Yield

Conditions & References

84 %

Stage 1: With oxygen, Time= 7h, T= 100 °C , p= 760.051Torr Stage 2: With sulfuric acid in acetone, Time= 0.0833333h, T= 56 °C , Further stages. Stec, Zbigniew; Orlinska, Beata; Jakubowski, BartLomiej; Zawadiak, Jan; International Journal of Chemical Kinetics; vol. 40; nb. 9; (2008); p. 527 - 532 View in Reaxys O

Rx-ID: 28166010 View in Reaxys 19/501 Yield

Conditions & References With oxygen, T= 245 °C , Mechanism, Temperature, Reagent/catalyst Hu, Jing; Xu, Kailai; Jia, Yunzhen; Lv, Yi; Li, Yubao; Hou, Xiandeng; Analytical Chemistry; vol. 80; nb. 21; (2008); p. 7964 - 7969 View in Reaxys

O O

Rx-ID: 28212011 View in Reaxys 20/501 Yield

Conditions & References

94 %Spectr., 5 %Spectr., 95 %Spectr.

With trifluorormethanesulfonic acid in chloroform-d1, T= 20 °C Liu, Yuanhong; Zhou, Shaolin; Li, Guijie; Yan, Bin; Guo, Shenghai; Zhou, Yebing; Zhang, Hao; Wang, Peng George; Advanced Synthesis and Catalysis; vol. 350; nb. 6; (2008); p. 797 - 801 View in Reaxys

O O

N H

N O

Rx-ID: 28662914 View in Reaxys 21/501 Yield

Conditions & References T= 140 °C , Kinetics, Temperature Platonova; Akhmetshin; Kossoi; Vdovets; Laskin; Malin; Sitdikov; Russian Journal of Applied Chemistry; vol. 81; nb. 10; (2008); p. 1808 - 1812 View in Reaxys

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O O

N H

H N

N H

Rx-ID: 28662916 View in Reaxys 22/501 Yield

Rx-ID: 10782426 View in Reaxys 23/501 Yield

Conditions & References 15 :EXAMPLE 15 To a 300 mL autoclave was added 0.396 g (1.5 mmol) of RhCl3.3H2O, 112.0 g (0.507 mol) of Nmethylpyridinium iodide, 30.0 g (0.5 mol) of acetic acid, and 74.0 g (1.0 mol) of methyl acetate. The mixture was heated to 190° C. under 17.2 barg (250 psig) of 5percent hydrogen in carbon monoxide. Upon reaching 190° C. the pressure was adjusted to 51.7 barg (750 psig) using 5percent hydrogen in CO. The temperature and pressure were maintained for 5 hours using 5percent hydrogen in CO as needed to maintain pressure. After 5 hours, the reaction was cooled, vented, and the product transferred to a sample bottle. GC analysis of the product showed that the mixture contained 1.31percent methyl acetate, 19.55percent acetic anhydride, 32.40percent acetic acid, and 1.70percent of ethylidene diacetate (1,1-diacetoxyethane). No methyl iodide was detected in the product by GC analysis. This example demonstrates that the process is applicable to the synthesis of acetic anhydride using methyl acetate as the carbonylation feedstock. With hydrogen, 1-methylpyridinium iodide, Rhodium trichloride, Time= 5h, T= 190 °C , p= 13689.1 - 39547.2Torr , Product distribution / selectivity Patent; EASTMAN CHEMICAL COMPANY; US2007/293695; (2007); (A1) English View in Reaxys 2H

O O

HO 2H

HO O

Rx-ID: 11057643 View in Reaxys 24/501 Yield

Conditions & References Stage 1:T= 140 °C Stage 2: With water, Time= 0.25h, T= 150 °C , Further stages. Title compound not separated from byproducts. Perrin, Charles L.; Dong, Yanmei; Journal of the American Chemical Society; vol. 129; nb. 14; (2007); p. 4490 4497 View in Reaxys O

Rx-ID: 25754595 View in Reaxys 25/501 Yield

Conditions & References 3 :Example 3; This example illustrates the formation of methyl acetate and acetic anhydride in the vapor phase over a catalyst dissolved in a non-volatile liquid. The example also shows the effect of adding small amounts of hydrogen to the carbon monoxide feed.Carbon monoxide (20 SCCM) was fed to the reactor described in Example 2 to prevent the liquid components from running out through the frit in the base of the reactor. The reactor then was charged with 1-butyl-3-methylimidazolium iodide ionic liquid (14.45 g, 10 mL, 0.054 mole), and a solution of rhodium trichloride hydrate (83.7 mg, 40.01percent Rh, 0.32 mmole) in methanol (5 mL) was added. Additional methanol (5 mL in portions) was used to rinse any residual rhodium solution into the reactor. The reactor was pressurized to 16.6 barg with carbon monoxide and then heated to 190° C. The carbon monoxide feed to the reactor was set for 120 SCCM. Prior to performing the dimethyl carbonate carbonylation, a methanol carbonylation and then a dimethyl ether carbonylation were performed under conditions similar to those used for the subsequent dimethyl carbonate carbonylation. As

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a result of these two preliminary reactions, the entire reactor system was free of methanol when the dimethyl carbonate carbonylation was started. A liquid mixture containing molar ratio=1.0 dimethyl carbonate/0.39 acetic acid/0.11 methyl iodide (density=1.127 g/mL) was fed to the vaporizer at 0.10 mL/minute along with the 120 SCCM carbon monoxide. The catalyst solution temperature rose and eventually leveled out at 193° C. Sample 1 (5.75 g) of the condensate was taken after one hour, and it contained the following components: 11.97percent methyl iodide, 0.01percent acetone, 31.55percent methyl acetate, 0percent dimethyl carbonate, 0percent methanol, 0percent water, 38.83percent acetic acid, 14.86percent acetic anhydride and 0.07percent ethylidene diacetate. The dimethyl carbonate conversion was 100percent and the net acetyl production rate was 6.05 moles/L catalyst solution-hour.The experiment was continued for an additional hour, and sample 2 (5.84 g) of liquid condensate taken contained the following components: 12.65percent methyl iodide, 0percent acetone, 41.35percent methyl acetate, 0percent dimethyl carbonate, 0percent methanol, 0percent water, 33.09percent acetic acid, 10.2percent acetic anhydride and 0percent ethylidene diacetate. The dimethyl carbonate conversion was 100percent, and the net acetyl production rate was 5.85 moles/L catalyst solution-hour. The reaction was continued producing methyl acetate and acetic anhydride under these conditions for an extended period of time during which the catalyst activity appeared to decline slightly, level out and then increase slightly as shown in the following Table wherein Sampling Time is the hours under reaction conditions between samples and the Space Time Yield is the moles of acetyl produced per liter of catalyst solution per hour. With acetic acid, methyl iodide, Rhodium trichloride in methanol, 1-butyl-3-methylimidazolium iodide ionic liquid, Time= 1 - 16h, T= 190 - 193 °C , Vapor phase, Product distribution / selectivity Patent; Eastman Chemical Company; US7253304; (2007); (B1) English View in Reaxys 3 :Example 3; This example illustrates the formation of methyl acetate and acetic anhydride in the vapor phase over a catalyst dissolved in a non-volatile liquid. The example also shows the effect of adding small amounts of hydrogen to the carbon monoxide feed.Carbon monoxide (20 SCCM) was fed to the reactor described in Example 2 to prevent the liquid components from running out through the frit in the base of the reactor. The reactor then was charged with 1-butyl-3-methylimidazolium iodide ionic liquid (14.45 g, 10 mL, 0.054 mole), and a solution of rhodium trichloride hydrate (83.7 mg, 40.01percent Rh, 0.32 mmole) in methanol (5 mL) was added. Additional methanol (5 mL in portions) was used to rinse any residual rhodium solution into the reactor. The reactor was pressurized to 16.6 barg with carbon monoxide and then heated to 190° C. The carbon monoxide feed to the reactor was set for 120 SCCM. Prior to performing the dimethyl carbonate carbonylation, a methanol carbonylation and then a dimethyl ether carbonylation were performed under conditions similar to those used for the subsequent dimethyl carbonate carbonylation. As a result of these two preliminary reactions, the entire reactor system was free of methanol when the dimethyl carbonate carbonylation was started. A liquid mixture containing molar ratio=1.0 dimethyl carbonate/0.39 acetic acid/0.11 methyl iodide (density=1.127 g/mL) was fed to the vaporizer at 0.10 mL/minute along with the 120 SCCM carbon monoxide. The catalyst solution temperature rose and eventually leveled out at 193° C. Sample 1 (5.75 g) of the condensate was taken after one hour, and it contained the following components: 11.97percent methyl iodide, 0.01percent acetone, 31.55percent methyl acetate, 0percent dimethyl carbonate, 0percent methanol, 0percent water, 38.83percent acetic acid, 14.86percent acetic anhydride and 0.07percent ethylidene diacetate. The dimethyl carbonate conversion was 100percent and the net acetyl production rate was 6.05 moles/L catalyst solution-hour.The experiment was continued for an additional hour, and sample 2 (5.84 g) of liquid condensate taken contained the following components: 12.65percent methyl iodide, 0percent acetone, 41.35percent methyl acetate, 0percent dimethyl carbonate, 0percent methanol, 0percent water, 33.09percent acetic acid, 10.2percent acetic anhydride and 0percent ethylidene diacetate. The dimethyl carbonate conversion was 100percent, and the net acetyl production rate was 5.85 moles/L catalyst solution-hour. The reaction was continued producing methyl acetate and acetic anhydride under these conditions for an extended period of time during which the catalyst activity appeared to decline slightly, level out and then increase slightly as shown in the following Table wherein Sampling Time is the hours under reaction conditions between samples and the Space Time Yield is the moles of acetyl produced per liter of catalyst solution per hour. With hydrogen, acetic acid, methyl iodide, Rhodium trichloride in methanol, 1-butyl-3-methylimidazolium iodide ionic liquid, Time= 2 - 5h, T= 190 - 193 °C , Vapor phase, Product distribution / selectivity Patent; Eastman Chemical Company; US7253304; (2007); (B1) English View in Reaxys

Rx-ID: 638787 View in Reaxys 26/501

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Yield

Conditions & References Keten oder Keten enthaltende Gase, wie sie bei der thermischen Zersetzung von Aceton erhalten werden Patent; Eschenbach; DE663507; (1935); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 150 View in Reaxys Patent; Roehm and Haas Co.; US1898687; (1931) View in Reaxys Patent; Carbide and Carbon Chem.Corp.; DE646408; (1933); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 24; p. 68 View in Reaxys gewinnt man Keten durch thermische Zersetzung von Essigsaeure an Katalysatoren, wie z.B.Phosphorsaeure, Phosphaten oder Phosphorsaeureestern Patent; I.G.Farbenind.; US1909816; (1930) View in Reaxys Patent; I.G.Farbenind.; US1982153; (1930) View in Reaxys Patent; I.G.Farbenind.; DE566451; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 364,19 361 View in Reaxys Patent; I.G.Farbenind.; DE571362; (1930) View in Reaxys Patent; I.G.Farbenind.; DE535046; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 759,19 363 View in Reaxys Patent; I.G.Farbenind.; DE565460; (1930) View in Reaxys Patent; Consort.elektrochem.Ind.; US2101868; (1934) View in Reaxys Patent; Consort.elektrochem.Ind.; US2102159; (1935) View in Reaxys Patent; Consort.elektrochem.Ind.; DE685427; (1934); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 24; p. 64 View in Reaxys Patent; Consort.elektrochem.Ind.; DE618270; (1933); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 22; p. 112,113 View in Reaxys Patent; Consort.elektrochem.Ind.; DE634438; (1933) View in Reaxys Patent; Consort.elektrochem.Ind.; US1946707; (1927) View in Reaxys Patent; Consort.elektrochem.Ind.; GB279070; (1927) View in Reaxys Nicodemus in K.Winnacker;E.Weingaertner; View in Reaxys Patent; Konsort. f. elektrochem. Ind.; DE403863; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 259 View in Reaxys reagiert analog mit anderen Carbonsaeuren unter Bildung gemischter Saeureanhydride Hurd; Dull; Journal of the American Chemical Society; vol. 54; (1932); p. 3427,3430 View in Reaxys Patent; Eastman Kodak Co.; US2235561; (1937) View in Reaxys Hurd; Roe; Journal of the American Chemical Society; vol. 61; (1939); p. 3355,3357 View in Reaxys Hurd; Thomas; Journal of the American Chemical Society; vol. 55; (1933); p. 275,281 View in Reaxys Chiller train 14 condenses water and acetic acid from the hot furnace gases and feeds flasher 18 with the condensate, while the uncondensed output from the furnace is fed to anhydride reactor 16 as shown in FIG. 1. In reactor 16, the ketene is reacted with additional acetic to produce acetic anhydride. Crude anhydride is removed as liquid, while overhead may be further purified and recycled or otherwise utilized.

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Patent; Warner, R. Jay; US2006/41162; (2006); (A1) English View in Reaxys gewinnt man Keten durch thermische Zersetzung von Essigsaeure an Katalysatoren, wie z.B.Phosphorsaeure, Phosphaten oder Phosphorsaeureestern Sixt; ; vol. 6; (1955); p. 806 - 808 View in Reaxys Keten oder Keten enthaltende Gase, wie sie bei der thermischen Zersetzung von Aceton erhalten werden Sixt; ; vol. 6; (1955); p. 808 - 810 View in Reaxys

Rx-ID: 23491904 View in Reaxys 27/501 Yield

Conditions & References

87 %

106 :EXAMPLE 106; N-{5-[2-(4-BENZO[D]ISOTHIAZOL-3-YL-PIPERAZIN-1-YL)-ETHYL]- 1, 1, 3, 3-TETRAMETHYL-INDAN-2-YLl-MMETHYLACETAMIDE METHANESULFONATE; To a solution of {5-[2-(4-Benzo[d]isothiazol-3-ylpiperazin-1-yl)-ethyl]- 1,1, 3, 3-tetramethyl-indan-2-yl}-methylamine (free base, 900 mg, 2.00 mmol) in methylene chloride (20 mL) was added acetic anhydride (0.75 mL, 8.0 mmol) and triethylamine (1.67 mL, 6.00 mmol). The mixture was stirred at rt for 5 h, and quenched with water. The organic phase was separated, washed with water, brine, dried over Na2SO4, evaporated, and chromatographed (silica gel, 25: 1 CH2CI2/MeOH with 0.5percent Et3N) to provide the free base of N-{5- [2- (4-Benzo [dJisothiazol-3-yl-piperazin-1-yl)- ethyl]-1, 1,3, 3-tetramethyl-indan-2-yl}N-methylacetamide (800 mg, 82percent) as a pale yellow solid. N-{5-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)ethyl]-1, 1,3, 3-tetramethyl-indan-2-yl}-N-methylacetamide (free base, 792 mg, 1.61 mmol) was dissolved in ethyl acetate (10 mL), and then treated with CH3SO3H (2M in Et20,0. 81 mL, 1.62 mmol). The reaction mixture was stirred at rt for 15 min. The precipitate was collected by filtration and dried in a vacuum oven at 55 °C overnight to give N-{5-[2-(4- Benzo [dJisothiazol-3-yl-piperazin-1-yl)-ethyl]-1, 1,3, 3-tetramethyl-indan-2- yl}-N-methylacetamide methanesulfonate (809 mg, 87percent) as a white solid : mp 248-250 °C ;'H NMR (300 MHz, CDC13, Note: mixture of two rotamers) . 811. 60 (br s, 1 H), 7.88-7. 83 (m, 2H), 7.53 (t, J = 7.5 Hz, 1 H), 7.42 (t, J = 7.5 Hz, 1H), 7.18-6. 99 (m, 3H), 5.13 (s, 0.5 H), 4.19-3. 96 (m, 4.5 H), 3.70- 3. 67 (m, 2H), 3.33-3. 13 (m, 6H), 2.90 (s, 3H), 2,71 (s, 1.5H), 2.67 (s, 1.5H), 2.22 (s, 1. 5 H), 2.12 (s, 1. 5 H), 1.42 (s, 1.5H), 1.41 (s, 1.5H), 1.40 (s, 1.5H), 1.39 (s, 1.5H), 1.33 (s, 1.5H), 1.32 (s, 1.5H), 1.29 (s, 1.5H), 1.28 (s, 1.5H) ; ESI MS m/z 491 [C29H38N4OS + H] + ; Rf 0. 45 (20: 1 CH2CI2/ MeOH) ; HPLC >98. 1percent (AUC), tR = 14.00 min. Anal. Calc'd for C29H38N40S | CH3SO3H : C, 61.40 ; H, 7.21 ; N, 9.55. Found: C, 61.28 ; H, 7.31 ; N, 9.52 in diethyl ether, ethyl acetate, Time= 0.25h, T= 20 °C Patent; WARNER-LAMBERT COMPANY LLC?; WO2005/56540; (2005); (A1) English View in Reaxys

Rx-ID: 637406 View in Reaxys 28/501 Yield

Conditions & References Berechnungen zur Kinetik der Oxydation, Kinetics Heatley; Canadian Journal of Research, Section B: Chemical Sciences; vol. 19; (1941); p. 261 View in Reaxys With oxygen, copper diacetate, anhydrous cobalt diacetate in ethanol, acetic acid, T= 40 °C , other ethanol concentrations, other temperatures,, Product distribution Levush, S. S.; Kit, Yu. V.; Koval'skaya, A. M.; Prisyazhnyuk, Z. P.; Mulyava, M. P.; J. Appl. Chem. USSR (Engl. Transl.); vol. 63; nb. 3; (1990); p. 705 - 708,672 - 675 View in Reaxys

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Direct conversion of acetaldehyde into acetic acid was accomplished using conventional techniques (e.g. by catalytic oxidizing with atmospheric oxygen in the presence of a mixture of copper and cobalt acetates at 50°-60° C.). The oxidation yields a mixture of acetic acid and acetic anhydride (45:55), with a conversion level between 16 to 18percent and a total yield between 94 to 96percent. With oxygen, copper diacetate, anhydrous cobalt diacetate, T= 50 - 60 °C Patent; NEUROK LLC; US2004/82817; (2004); (A1) English View in Reaxys

O O

Rx-ID: 9719877 View in Reaxys 29/501 Yield

Conditions & References Time= 8h, T= 80 °C , Product distribution Voronkov; Trukhina; Vlasova; Russian Journal of Organic Chemistry; vol. 40; nb. 3; (2004); p. 357 - 359 View in Reaxys

O O

Rx-ID: 9741192 View in Reaxys 30/501 Yield

Conditions & References

52 %, 28 %

Time= 6h, T= 90 °C Voronkov; Trukhina; Vlasova; Russian Journal of Organic Chemistry; vol. 40; nb. 3; (2004); p. 357 - 359 View in Reaxys

Rx-ID: 23398784 View in Reaxys 31/501 Yield

Conditions & References 20; 21 : Examples 20-21 and comparative Example G-batch reactions for carbonylation of butadiene with acid to pentenoic acid via anhydride A 250 ml magnetically stirred autoclave was successively charged with 20 ml acetic acid, 40 ml diglyme, palladium acetate (0,25 mmol in Example 20 and 0,1 mmol in Example 21 and Comparative Example G), and 0.5 mmol of the respective ligand. In Examples 20 and 21, the same ligand was used as in Examples 1-13, and in Comparative Example G the same ligand was used as in Comparative Example A. The autoclave was then closed and evacuated and 10 ml butadiene was pumped IN. The autoclave was pressurized with CO to 4 MPa, sealed, heated to 135 °C and maintained at that temperature for 10 hours. After cooling the contents was analysed with GLC. The initial carbonylation rate was defined as for Examples 1-18 and Comparative Examples A-D. In Example 20 the butadiene conversion to pentenoic acid was >90percent while the acetic acid was converted to acetic anhydride for 35percent. The initial carbonylation rate was 400 mol/mol Pd/hr. In Example 21 the same conversions were measured as in Example 20 but the reaction rate was 900 mol/molPd/hr. In Comparative Example G the butadiene conversion to pentenoic acid was 15percent while the acetic acid was converted to acetic anhydride for 5percent. The reaction rate was 60 mol/mol Pd/hr. in diethylene glycol dimethyl ether, Time= 10h, T= 135 °C , p= 30003Torr , Conversion of starting material Patent; SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.; WO2004/103948; (2004); (A1) English View in Reaxys G : Examples 20-21 and comparative Example G-batch reactions for carbonylation of butadiene with acid to pentenoic acid via anhydride

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A 250 ml magnetically stirred autoclave was successively charged with 20 ml acetic acid, 40 ml diglyme, palladium acetate (0,25 mmol in Example 20 and 0,1 mmol in Example 21 and Comparative Example G), and 0.5 mmol of the respective ligand. In Examples 20 and 21, the same ligand was used as in Examples 1-13, and in Comparative Example G the same ligand was used as in Comparative Example A. The autoclave was then closed and evacuated and 10 ml butadiene was pumped IN. The autoclave was pressurized with CO to 4 MPa, sealed, heated to 135 °C and maintained at that temperature for 10 hours. After cooling the contents was analysed with GLC. The initial carbonylation rate was defined as for Examples 1-18 and Comparative Examples A-D. In Example 20 the butadiene conversion to pentenoic acid was >90percent while the acetic acid was converted to acetic anhydride for 35percent. The initial carbonylation rate was 400 mol/mol Pd/hr. In Example 21 the same conversions were measured as in Example 20 but the reaction rate was 900 mol/molPd/hr. In Comparative Example G the butadiene conversion to pentenoic acid was 15percent while the acetic acid was converted to acetic anhydride for 5percent. The reaction rate was 60 mol/mol Pd/hr. in diethylene glycol dimethyl ether, Time= 10h, T= 135 °C , p= 30003Torr , Conversion of starting material Patent; SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.; WO2004/103948; (2004); (A1) English View in Reaxys O

O H

Rx-ID: 23656510 View in Reaxys 32/501 Yield

Conditions & References 1; 2; 3 Product distribution / selectivity Patent; BASF AKTIENGESELLSCHAFT; WO2004/37762; (2004); (A1) German View in Reaxys

Rx-ID: 23740901 View in Reaxys 33/501 Yield

Conditions & References 8.1; 8.2; 8.3; 8.4 :This example illustrates the production of acetic anhydride (Ac2O) by the carbonylation of methyl acetate in the presence of rhodium and 1-butyl-3-methylimidazolium iodide. This example also illustrates that the catalyst system maintains good activity after being used for both ethanol and methyl acetate carbonylation. The reactor containing the catalyst system of Example 7 was used in this example. After the experiment of Example 7-4 was completed, the furnace temperature was lowered to 180° C., and the weight ratio methanol/methyl iodide=70/30 was fed at 0.13 mL/minute along with 150 SCCM CO for 5.33 hours. Pressure was maintained at 200 psig (13.8 barg). The gas feed was then changed to 150 SCCM CO and 8 SCCM hydrogen and a liquid feed consisting of methyl acetate/acetic acid/methyl iodide in a weight ratio of 65/21/14 having a density=1.0 g/mL was fed at 0.13 mL/ minute. These conditions were maintained for a portion of an 18.83-hour time period before collecting the product samples shown in Table 10 due to a mechanical failure in the liquid feed pump although the CO-hydrogen flow was maintained at 200 psig (13.8 barg) during the entire 18.83 your period. The liquid feed pump was replaced before the samples in Table 10 were collected. [0057] Liquid product samples were analyzed by gas chromatography. An accurately-weighed one-gram sample was diluted with 5 mL of an internal standard solution prepared from dilution of 20 mL p-xylene to 500 mL with acetonitrile. One microliter of this mixture was injected onto a 30M.x.0.25 mm.x.0.25 micron DB 1701 column under the following conditions using 14.5 psig (1 barg) helium carrier gas flowing at 3.0 mL/ minute. Injector parameters: T=250° C., split flow=100 mL/minute, split ratio=75:1, purge=2 mL/minute; Detector parameters: flame ionization, T=250° C.; Oven parameters: 3 minutes at 35° C., 15° C./minute to 250° C., 250° C. for 0 minutes. [0058] Examples 8-1 and 8-2 were performed with the furnace temperature at 180° C., liquid feed rate=0.13 mL/minute with gas flow rate=150 SCCM CO and 8 SCCM hydrogen. Example 8-3 was performed with the furnace temperature at 180° C., liquid feed rate=0.25 mL/minute and gas flow rate=300 SCCM CO and 15 SCCM hydrogen. Example 8-4 was performed with the furnace temperature at 190° C., liquid feed rate=0.25 mL/minute and gas flow rate=300 SCCM CO and 15 SCCM hydrogen. The results are summarized in Table 10. With hydrogen, Rhodium trichloride, [bmim][I], Time= 3.17 - 19.5h, T= 180 °C , p= 11103.3Torr , Product distribution / selectivity Patent; Charles, Gerald; Michelle, Regina; US2003/212295; (2003); (A1) English

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View in Reaxys O

Rx-ID: 23742025 View in Reaxys 34/501 Yield

Conditions & References 9.1; 9.2; 9.3; 9.4; 9.5; 9.6 :This example illustrates the production of acetic anhydride (Ac2O) by the carbonylation of methyl acetate in the presence of palladium and 1-butyl-3-methylimidazolium iodide. The reactor of Example 1 was loaded with 1-butyl-3-methylimidazolium iodide (14.45 g, 10 mL) and a mixture of palladium acetate (73.1 mg, 0.325 mmol) dissolved in methyl acetate (3 mL). The reactor was pressurized to 200 psig (13.8 barg) with CO (20 SCCM) and heated to 180° C. The gas feed was then changed to 150 SCCM CO and 8 SCCM hydrogen and a liquid feed consisting of methyl acetate/acetic acid/methyl iodide in a weight ratio of 65/21/14 having a density=1.0 was fed at 0.13 mL/minute. Examples 9-1,9-2, 9-3, and 9-4 were performed under these conditions. Example 9-5 was performed using the same gas and liquid feed rates at a 190° C. furnace temperature. Example 9-6 was performed at 190° C. in the absence of hydrogen with the carbon monoxide and liquid feed rates unchanged. The results are summarized in Table 11. With hydrogen, palladium diacetate, [bmim][I], Time= 3 - 19.58h, T= 180 - 190 °C , p= 11103.3Torr , Product distribution / selectivity Patent; Charles, Gerald; Michelle, Regina; US2003/212295; (2003); (A1) English View in Reaxys 9.6 :This example illustrates the production of acetic anhydride (Ac2O) by the carbonylation of methyl acetate in the presence of palladium and 1-butyl-3-methylimidazolium iodide. The reactor of Example 1 was loaded with 1-butyl-3methylimidazolium iodide (14.45 g, 10 mL) and a mixture of palladium acetate (73.1 mg, 0.325 mmol) dissolved in methyl acetate (3 mL). The reactor was pressurized to 200 psig (13.8 barg) with CO (20 SCCM) and heated to 180° C. The gas feed was then changed to 150 SCCM CO and 8 SCCM hydrogen and a liquid feed consisting of methyl acetate/acetic acid/methyl iodide in a weight ratio of 65/21/14 having a density=1.0 was fed at 0.13 mL/minute. Examples 9-1,9-2, 9-3, and 9-4 were performed under these conditions. Example 9-5 was performed using the same gas and liquid feed rates at a 190° C. furnace temperature. Example 9-6 was performed at 190° C. in the absence of hydrogen with the carbon monoxide and liquid feed rates unchanged. The results are summarized in Table 11. , T= 190 °C , p= 11103.3Torr , Product distribution / selectivity Patent; Charles, Gerald; Michelle, Regina; US2003/212295; (2003); (A1) English View in Reaxys

O O

polyoxyethylene dipropylamine

O O

polyoxyethylene dipropylmaleamic acid Rx-ID: 25396499 View in Reaxys 35/501 Yield

Conditions & References Maleimidation: Maleimidation: Into a 1 liter four-necked flask equipped with a stirrer, a thermometer, a condenser, and a nitrogen-bubbling tube were charged 164 g of the polyoxyethylene dipropylamine and 325 ml of toluene and heated to 50°C to prepare a solution. To the solution was added 32 g of maleic anhydride, followed by stirring for 4 hours. The reaction mixture was cooled to 40°C, and a mixture of 800 ml of ethyl acetate and 800 ml of hexane was poured therein, followed by stirring for 30 minutes to crystallize. The crystals collected by filtration were again dissolved in 325 ml of toluene, a mixture of 800 ml of ethyl acetate and 800 ml of hexane was poured therein, followed by stirring for 30 minutes to crystallize. The crystals collected by filtration were dried to give 165 g of polyoxyethylene dipropylmaleamic acid, which was found to have a maleic anhydridecontent of 0.0018 wtpercent.

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Into a 1 liter four-necked flask equipped with a stirrer, a thermometer, a condenser, and a nitrogen-bubbling tube were charged 165 g of the resulting polyoxyethylene dipropylmaleamic acid, 500 ml of acetic anhydride, and 63 g of sodium acetate. The mixture was heated to 90°C, at which it was stirred for 3 hours to conduct reaction. After cooling to 50°C, the reaction mixture was filtered to remove sodium acetate, and the filtrate was concentrated at 90°C under reduced pressure of 0.3 kPa. The concentrate was dissolved in 360 ml of chloroform, and any insoluble matter was removed by filtration. A mixture of 1 liter of ethyl acetate and 1 liter of hexane was poured into the filtrate, followed by stirring for 30 minutes to crystallize. The crystals were collected by filtration. The crystals were again dissolved in 360 ml of chloroform and crystallized from a mixture of ethyl acetate (1 liter) and hexane (1 liter) by stirring for 30 minutes. in hexane, ethyl acetate, toluene Patent; NOF CORPORATION; EP1283233; (2003); (A1) English View in Reaxys

Rx-ID: 8889628 View in Reaxys 36/501 Yield

Conditions & References With nitrous acid methyl ester, methyl-nitrate, T= 24.85 °C , Heating, Product distribution, Kinetics Picquet-Varrault; Doussin; Durand-Jolibois; Carlier; Physical Chemistry Chemical Physics; vol. 3; nb. 13; (2001); p. 2595 - 2606 View in Reaxys Cl O

Rx-ID: 25471110 View in Reaxys 37/501 Yield

Conditions & References 6 : Preparation of 5-chloro-2-(2,4-dichlorophenoxy)phenol by Baever-Villiger oxidation with acetic anhydride/ H2O2 Example 6 Preparation of 5-chloro-2-(2,4-dichlorophenoxy)phenol by Baever-Villiger oxidation with acetic anhydride/H2O2 18 ml of acetic anhydride are mixed at -5° C. with 4.5 ml of 98percent sulfuric acid. 4.2 ml of 30percent hydrogen peroxide are added dropwise with very vigorous stirring at -5 to -3° C. in the course of 25 minutes. The milky emulsion is treated at -5° C. with 12.5 ml of methylene chloride, a clear solution being formed. This is then added with very vigorous stirring in the course of 3 minutes to a mixture of 7.9 g of the acetyl compound of the formula (102), 15 ml of methylene chloride, 18 ml of 100percent acetic acid and 13.5 ml of 98percent sulfuric acid, at a temperature of 0 to -5° C. The reaction mixture is two-phase and dark. The reaction is kept at 0 to 5° C. for one hour, then at 10° C. for 4 hours and at 15° C. for 1 hour. It is finally allowed to react to completion at 20° C. for 20 hours, the intermediately formed phenol ester of the formula (104) also being partially hydrolyzed to the phenol derivative of the formula (105). After destruction of the excess hydrogen peroxide, the methylene chloride is distilled out. For complete hydrolysis, the temperature is kept at 100° C. for 4 hours. The product is recovered via methylene chloride extraction. After distillation of the solvent, an oily residue of 7 g of the crude product of the formula (105) remains, which after customary purification yields the product with a melting point of 56 to 57° C. Patent; Ciba Specialty Chemicals Corporation; US6215029; (2001); (B1) English View in Reaxys

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O O

Rx-ID: 25471133 View in Reaxys 38/501 Yield

Conditions & References 9 : Ethyl 1-(tert-butyl)-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate. PREPARATION 9 Ethyl 1-(tert-butyl)-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate. A solution of 2.36 g of ethyl 3-(2-fluoro-5-iodophenyl)-3-oxopropanoate from Preparation No. 8, 2.0 mL of triethyl orthoformate, and 15 mL of acetic anhydride is refluxed under argon for 2 hours, then the solvents are distilled off under reduced pressure. Patent; Pharmacia and Upjohn Company; US6248736; (2001); (B1) English View in Reaxys 30 : Ethyl 1-(tert-butyl)-6-iodo4-oxo-1,4-dihydro-3-quinolinecarboxylate Preparation 30 Ethyl 1-(tert-butyl)-6-iodo4-oxo-1,4-dihydro-3-quinolinecarboxylate A solution of 2.36 g of ethyl 3-(2-fluoro-5-iodophenyl)-3-oxopropanoate from Preparation No. 29, 2.0 mL of triethyl orthoformate, and 15 mL of acetic anhydride is refluxed under argon for 2 h, then the solvents are distilled off under reduced pressure. Patent; Pharmacia and Upjohn Company; US6248739; (2001); (B1) English View in Reaxys 56 : Ethyl 1-(4-Morpholinyl)-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate Preparation 56 Ethyl 1-(4-Morpholinyl)-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate Ethyl 3-[2-fluoro-5-(4-morpholinylmethyl)phenyl]-3-oxopropanoate (10.0 g) of Preparation No. 55, triethylorthoformate (10.8 mL) and acetic anhydride (10.7 mL) are combined in a flask equipped with a Dean-Stark trap and condenser. The reaction is heated to 150° C. for 3.5 hours. The excess acetic anhydride and triethylorthoformate are distilled off at 100° C. and 0.2 torr leaving a burgundy oil containing a mixture of E- and Z-isomers of ethyl-3-ethoxy-2-[2-fluoro-5-(4-morpholinylmethyl)benzoyl]-2-propenoate. Patent; Pharmacia and Upjohn Company; US6248739; (2001); (B1) English View in Reaxys

N OH

4 HBr

O N

NH 2

OH NH 2

Rx-ID: 8763647 View in Reaxys 39/501 Yield

Conditions & References T= 24.85 °C , Oxidation, Kinetics, Further Variations: var. conc. of hexamethylenetetramine-bromine Gangwani; Sharma; Banerji; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 39; nb. 4; (2000); p. 436 - 438 View in Reaxys

N O

H 2N

N NH O

Rx-ID: 24431487 View in Reaxys 40/501 Yield

Conditions & References 186 : 1-[2-(4-Acetamidophenoxy)ethyl]-4-(4-methylbenzyl)piperidine STR222 EXAMPLE 186

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1-[2-(4-Acetamidophenoxy)ethyl]-4-(4-methylbenzyl)piperidine STR222 From a solution of 1-[2-(4-aminophenoxy)ethyl]-4-(4-methylbenzyl)piperidine (1.22 g, 3.72 mmol) in CH2 Cl2 (20 mL) with acetic anhydride (2 mL) at r.t. was obtained 1.27 g (85percent) of the title compound as a white powder. 1 H NMR (CDCl3): 1.25-1.38 (m, 2H), 1.42-1.55 (m, 1H), 1.62-1.66 (m, 2H), 2.00-2.07 (m, 2H), 2.152 (s, 3H), 2.315 (s, 3H), 2.493 (d, 2H, J=7), 2.754 (t, 2H, J=6), 2.94-2.98 (m, 2H), 4.065 (t, 2H, J=6), 6.847 (d, 2H, J=9), 7.055 (AB, 4H, J=9), 7.363 (d, 2H, J=9). in dichloromethane Patent; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); (A1) English View in Reaxys O HO

H 2N

Rx-ID: 24431488 View in Reaxys 41/501 Yield

Conditions & References 188 : 1-(3-Acetamido-4-hydroxyphenoxy)ethyl-4-(4-methylbenzyl)piperidine STR224 EXAMPLE 188 1-(3-Acetamido-4-hydroxyphenoxy)ethyl-4-(4-methylbenzyl)piperidine STR224 From a solution of 1-(2-(3-amino-4-hydroxyphenoxy)ethyl)-4-(4-methylbenzyl)piperidine (950 mg, 2.8 mmol) in CH2 Cl2 (20 mL) with acetic anhydride (2 mL) was obtained 930 mg (87percent) of 1-(2-(3-acetarmido-4-hydroxy-phenoxy)ethyl)-4-(4-methylbenzyl)piperidine as a viscous oil. 1 H NMR (CDCl3): 1.30-1.42 (m, 2H), 1.48-1.56 (m, 1H), 1.64-1.68 (m, 2H), 2.02-2.09 (m, 2H), 2.246 (s, 3H), 2.320 (s, 3H), 2.500 (d, 2H, J=7), 2.731 (t, 2H, J=6), 2.99-3.03 (m, 2H), 3.956 (t, 2H, J=6), 6.530 (dd, 1H, J=9; 3), 6.76-6.79 (m, 2H), 7.027 (d, 2H, J=8), 7.090 (d, 2H, J=8), 7.830 (bs, 1H). in dichloromethane Patent; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); (A1) English View in Reaxys

Rx-ID: 693113 View in Reaxys 42/501 Yield

Conditions & References With pyridine, benzene, folgendes Eintropfen von wenig Wasser Adkins; Thompson; Journal of the American Chemical Society; vol. 71; (1949); p. 2242 View in Reaxys With BaO, T= 100 °C Gal; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 56; (1863); p. 361; Justus Liebigs Annalen der Chemie; vol. 128; (1863); p. 127 View in Reaxys With lead (II) nitrate Lachowicz; Chemische Berichte; vol. 17; (1884); p. 1283 View in Reaxys With silver nitrate Armstrong; Lapworth; ; vol. 9; p. 255 View in Reaxys With potassium nitrate, T= 25 °C Diels; Okada; Chemische Berichte; vol. 44; (1911); p. 3335

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View in Reaxys 3 : Synthesis of diacetoxydialkoxysilanes with acetic anhydride Example 3 Synthesis of diacetoxydialkoxysilanes with acetic anhydride 221 g (1.3 mol) of SiCl4 are introduced into a flask which is equipped with internal thermometer, dropping funnel, stirrer and distillation apparatus and, while stirring, 530 g (5.2 mol) of acetic anhydride and 4 g of acetic acid were added. The mixture is then stirred at 45°-50° C. for 1 h and subsequently 404 g of acetyl chloride are distilled out (at 50°-58° C.). Then 2.6 mol of the appropriate alcohol are in each case added to the residue. The mixture is then stirred at 50° C. for 1 h and worked up by vacuum distillation. The results are compiled in Table 1. With SiCl4, acetic anhydride, acetic acid Patent; Friedrich; Holger; Leutner; Bernd; Mronga; Norbert; Schmid; Raimund; US5817853; (1998); (A1) English View in Reaxys

O O

O H H

O H

Rx-ID: 5082765 View in Reaxys 43/501 Yield

Conditions & References With sulfuric acid, T= 60 °C , Hydrolysis, Equilibrium constant, Further Variations: Temperatures Bulychev; Pharmaceutical Chemistry Journal; vol. 32; nb. 6; (1998); p. 331 - 332 View in Reaxys

O Cl

–O

Cl P

Na +

O P

P O

Cl Cl

P O

Cl Cl

Rx-ID: 5143578 View in Reaxys 44/501 Yield

Conditions & References in acetonitrile, Time= 24h, Mechanism Khailova; Shaimardanova; Pudovik; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2311 - 2312 View in Reaxys

O O

N N

Rx-ID: 24664116 View in Reaxys 45/501 Yield 74%

Conditions & References 2 : Preparation of 5-methoxy-1,3,4-triphenyl-1,2,4-(5H)-triazoline with formic acid/acetic anhydride

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EXAMPLE 2 Preparation of 5-methoxy-1,3,4-triphenyl-1,2,4-(5H)-triazoline with formic acid/acetic anhydride 220 g (0.75 mol) of N1,N3 -diphenylbenzamidrazone were added to a mixture of 1100 g of acetic anhydride and 630 g of formic acid, after which the glyceride was stirred for 12 h at 25° C. After stripping off the solvent, 346 g of a yellow viscous resin remained. After dissolving the resin in 1000 ml of methanol, 750 ml (4 mol) of 30percent strength sodium methoxide solution were added with ice-cooling, and the mixture was stirred for a further 2 h. The solid was filtered off with suction, washed with methanol and recrystallized from methanol. 5-Methoxy-1,3,4-triphenyl-1,2,4-(5H)-triazoline was obtained in 74percent yield as a pale yellow, crystalline solid (m.p.: 114° C.). Patent; BASF Aktiengesellschaft; US5840894; (1998); (A1) English View in Reaxys

–O

K+

O– K+

Rx-ID: 3000073 View in Reaxys 46/501 Yield

Conditions & References With 18-crown-6 ether in benzene, T= 20 °C , other temperatures, Rate constant Kovach, Ildiko M.; Journal of Organic Chemistry; vol. 47; nb. 12; (1982); p. 2235 - 2241 View in Reaxys With 18-crown-6 ether in acetonitrile, T= 20 °C , ΔH(excit.), ΔS(excit.), ΔG0, Thermodynamic data, Equilibrium constant Kovach, Ildiko M.; Journal of Organic Chemistry; vol. 47; nb. 12; (1982); p. 2235 - 2241 View in Reaxys With 18-crown-6 ether in acetonitrile, T= 20 °C , other substituted phenol acetates, various solvents and temperatures, Mechanism Kovach, Ildiko M.; Journal of Organic Chemistry; vol. 47; nb. 12; (1982); p. 2235 - 2241 View in Reaxys With 18-crown-6 ether in chlorobenzene, T= 25 °C , Rate constant, Equilibrium constant Ba-Saif, Salem A.; Maude, Antony B.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1994); p. 2395 - 2400 View in Reaxys in acetonitrile, T= 25 °C , Kinetics, Equilibrium constant Maude, Antony B.; Williams, Andrew; Journal of the Chemical Society. Perkin Transactions 2; nb. 2; (1997); p. 179 - 183 View in Reaxys

–O

O O

–O

K+

Rx-ID: 4162991 View in Reaxys 47/501 Yield

Conditions & References With 18-crown-6 ether in chlorobenzene, T= 25 °C , Rate constant, Equilibrium constant Ba-Saif, Salem A.; Maude, Antony B.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1994); p. 2395 - 2400 View in Reaxys in acetonitrile, T= 25 °C , Kinetics, Equilibrium constant

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Maude, Antony B.; Williams, Andrew; Journal of the Chemical Society. Perkin Transactions 2; nb. 2; (1997); p. 179 - 183 View in Reaxys O O

–O

O–

K+

O N

K+

Rx-ID: 4163164 View in Reaxys 48/501 Yield

O O

K+

O–

K+

Rx-ID: 4164396 View in Reaxys 49/501 Yield

–O

O– Cl

K+

Rx-ID: 4166011 View in Reaxys 50/501 Yield

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Rx-ID: 4669103 View in Reaxys 51/501 Yield

Conditions & References

With ozone in dichloromethane, T= -75 °C , Yields of byproduct given Griesbaum, Karl; Dong, Yuxiang; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 6; (1997); p. 575 - 577 View in Reaxys

54 % Spectr., 21 % Spectr., 8% Spectr., 9 % Spectr.

With ozone, tetrachloroethane, 1,1,2,2- in dichloromethane-d2, T= -75 °C , var. solvent, Product distribution, Mechanism Griesbaum, Karl; Dong, Yuxiang; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 6; (1997); p. 575 - 577 View in Reaxys

O O

Rx-ID: 4710694 View in Reaxys 52/501 Yield

Conditions & References With triphenylphosphine in chloroform-d1, Time= 48h, Ambient temperature, Product distribution Griesbaum, Karl; Liu, Xuejun; Dong, Yuxiang; Tetrahedron; vol. 53; nb. 15; (1997); p. 5463 - 5470 View in Reaxys O

Rx-ID: 4761023 View in Reaxys 53/501 Yield

Conditions & References

71 %, 17 %, 5 %, 7 %

With ozone in dichloromethane, T= -100 °C Griesbaum, Karl; Dong, Yuxiang; McCullough, Kevin J.; Journal of Organic Chemistry; vol. 62; nb. 18; (1997); p. 6129 - 6136 View in Reaxys

H O

NH 2

O O

Rx-ID: 4778269 View in Reaxys 54/501 Yield

Conditions & References With pyridine, ozone, 1) CH2Cl2, -100 deg C; 2) methanol, -75 deg C, 5 d, Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given Griesbaum, Karl; Dong, Yuxiang; McCullough, Kevin J.; Journal of Organic Chemistry; vol. 62; nb. 18; (1997); p. 6129 - 6136 View in Reaxys

O O

Rx-ID: 4784960 View in Reaxys 55/501

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Yield

Conditions & References With ozone in dichloromethane, T= -100 °C Griesbaum, Karl; Dong, Yuxiang; McCullough, Kevin J.; Journal of Organic Chemistry; vol. 62; nb. 18; (1997); p. 6129 - 6136 View in Reaxys O F

O O N

N N

Rx-ID: 24595418 View in Reaxys 56/501 Yield

Conditions & References 16 : Racemization of FTAP with Sulfuric Acid and Acetic Anhydride EXAMPLE 16 Racemization of FTAP with Sulfuric Acid and Acetic Anhydride To S-diastereoisomer of FTAP (94.5percent ee, 5.10 g, 20.0 mmol) were added acetic anhydride (10.0 g) and further sulfuric acid (1.06 ml) at room temperature, and the mixture was stirred at 50° C. for 3 h, and then at 60° C. for 3h. After the reaction mixture was basified with sodium carbonate solution, the resulting mixture was extracted with ethyl acetate (30 ml*2). After the extract was dried over anhydrous sodium sulfate, the solvent was distilled off in vacuo to give 5.26 g of yellow oily material. Purification of this oily material by silica gel column chromatography gave 4.47 g (recovery 66percent) of 1,2-diacetoxy-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propane with optical purity of 69.8percent ee. Patent; Daicel Chemical Industries, Ltd.; US5702928; (1997); (A1) English View in Reaxys

Rx-ID: 4478904 View in Reaxys 57/501 Yield

Conditions & References

48 % Spectr., 52 % Spectr.

With ozone in dichloromethane, T= -75 °C , var. of solvent, Product distribution Griesbaum, Karl; Schlindwein, Konrad; Bettinger, Herbert; Advanced Synthesis and Catalysis; vol. 338; nb. 4; (1996); p. 307 - 310 View in Reaxys

O O

Rx-ID: 4507439 View in Reaxys 58/501 Yield

Conditions & References in gas, Irradiation, var. laser pulse irradiation lines; var. pressures, Product distribution, Mechanism Khachatryan, Lavrenti; Fajgar, Radek; Haas, Yehuda; Pola, Josef; Journal of the Chemical Society. Perkin Transactions 2; vol. 9; (1996); p. 1981 - 1984 View in Reaxys

–O

Na +

H2O Rx-ID: 6214082 View in Reaxys 59/501

Yield

Conditions & References With zeolite NaY, Product distribution Pope, Christopher G.; Journal of the Chemical Society - Faraday Transactions; vol. 92; nb. 19; (1996); p. 3647 3651

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View in Reaxys OH

O O

CO2

Rx-ID: 7072249 View in Reaxys 60/501 Yield

Conditions & References With (CO)4(palladium)4(acetate)4, Time= 1.5h, other object of study: methanol, isopropanol, Product distribution, Mechanism Chernysheva; Stromnova; Vargafiik; Moiseev; Russian Chemical Bulletin; vol. 45; nb. 10; (1996); p. 2327 - 2330 View in Reaxys OH

[Pd(CO)(OAc)]4 O

O O

Rx-ID: 8515607 View in Reaxys 61/501 Yield

Conditions & References Time= 0.5h, T= 20 °C , alcoholysis, Further byproducts given Chernysheva; Stromnova; Vargaftik; Moiseev; Doklady Chemistry; vol. 348; nb. 4-6; (1996); p. 159 - 161 View in Reaxys N O

Rx-ID: 24519760 View in Reaxys 62/501 Yield

Conditions & References 6 : EXAMPLE 6 EXAMPLE 6 For the synthesis of 4-[4-(p-chlorophenyl)-4-acetoxypiperidinyl]-4'-fluorobutyrophenone (UCSF6), acetic anhydride (3 mL) and 4-dimethylaminopyridine (45 mg) were added to a suspension of haloperidol (100 mg) in 15 mL of CH2 Cl2. Patent; The Regents of the University of California; US5583000; (1996); (A1) English View in Reaxys

N+

–O

I–

O (v2)

O 2+Zr

Rx-ID: 24589548 View in Reaxys 63/501 Yield

Conditions & References 33 : EXAMPLE 33 EXAMPLE 33 This Example was carried out as described in Example 31, except that LiI was not added and, instead, zirconyl diacetate (200 mol percent to rhodium) and a tetraammonium salt, i.e., tetraethylammonium iodide (2000 mol percent to rhodium) were added as promoters; and the reaction was conducted at 165° C. and 800 psi for 2 hrs. The yield of acetic anhydride was about 90percent. Patent; Korea Institute of Science and Technology; US5488143; (1996); (A1) English View in Reaxys

O C

Rx-ID: 4467528 View in Reaxys 64/501

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Yield

Conditions & References With Rhodium trichloride, hydrogen, triphenylphosphine, methyl iodide in acetic acid, Time= 4h, T= 169.9 °C , p= 41868.4Torr , var. catalyst precursors, var. ligand, var. temp., var. time, var. solvent, var. reagents ratio, Product distribution Kelkar, A. A.; Chaudhari, R. V.; Journal of Catalysis; vol. 157; nb. 2; (1995); p. 334 - 343 View in Reaxys

Rx-ID: 25412853 View in Reaxys 65/501 Yield

Conditions & References 11 : Example 11 Example 11 A mixture of 1088 parts (8 moles) of pentaerythritol, 1360 parts (8 moles) of a commercial methyl ester of an acid mixture comprising about 55percent of C8, 40percent of C1 0 and 4percent of C6 acids ('CE810 Methyl Ester', Procter and Gamble), 816 parts of acetic anhydride and 10 parts of paratoluene sulfonic acid is prepared and heated to reflux. About 500 parts of a volatile material are removed. Patent; THE LUBRIZOL CORPORATION; EP646638; (1995); (A2) English View in Reaxys O

O F

F F

Rx-ID: 1938554 View in Reaxys 66/501 Yield

Conditions & References With tin(II) trifluoromethanesulfonate in dichloromethane-d2, Title compound not separated from byproducts Miyashita, Mitsutomo; Shiina, Isamu; Mukaiyama, Teruaki; Bulletin of the Chemical Society of Japan; vol. 67; nb. 1; (1994); p. 210 - 215 View in Reaxys

–O

O K+

–O

O O

N N O

K+

Rx-ID: 3869128 View in Reaxys 67/501 Yield

Conditions & References With 18-crown-6 ether in benzene, T= 10 °C , other temperatures; ΔH(excit.), Rate constant, Thermodynamic data Kovach, Ildiko M.; Journal of Organic Chemistry; vol. 47; nb. 12; (1982); p. 2235 - 2241 View in Reaxys With 18-crown-6 ether in acetonitrile, T= 20 °C , ΔH(excit.), ΔS(excit.), ΔG0, Equilibrium constant, Thermodynamic data Kovach, Ildiko M.; Journal of Organic Chemistry; vol. 47; nb. 12; (1982); p. 2235 - 2241 View in Reaxys With 18-crown-6 ether in chlorobenzene, T= 25 °C , Rate constant, Equilibrium constant Ba-Saif, Salem A.; Maude, Antony B.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1994); p. 2395 - 2400 View in Reaxys

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O O

O racemate

Rx-ID: 4015528 View in Reaxys 68/501 Yield

Conditions & References in benzene-d6, T= 60 °C , Rate constant Baumstark, A. L.; Vasquez, P. C.; Chen, Y.-X.; Journal of Organic Chemistry; vol. 59; nb. 22; (1994); p. 6692 6696 View in Reaxys Cl –O

O–

K+

O Cl

Rx-ID: 4160595 View in Reaxys 69/501 Yield

Conditions & References With 18-crown-6 ether in chlorobenzene, T= 25 °C , Rate constant Ba-Saif, Salem A.; Maude, Antony B.; Williams, Andrew; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1994); p. 2395 - 2400 View in Reaxys

–O

O–

O K+

O O

K+

N O

Rx-ID: 4161263 View in Reaxys 70/501 Yield

Cl O

–O

K+

O–

K+

Rx-ID: 4162350 View in Reaxys 71/501 Yield

–O

O–

K+

Cl Cl

K+

Rx-ID: 4163160 View in Reaxys 72/501

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Yield

–O

K+

O– K+

Cl Cl Cl

Rx-ID: 4166012 View in Reaxys 73/501 Yield

O O

Rx-ID: 2346851 View in Reaxys 74/501 Yield

Conditions & References

3 %, 7 %, 13 %

With pyridine, oxygen, 1) AcOEt, 20 h, irradiation, Yield given. Multistep reaction Tateba, Hideki; Morita, Kouzou; Kameda, Wataru; Tada, Masahiro; Bioscience, Biotechnology, and Biochemistry; vol. 57; nb. 2; (1993); p. 220 - 226 View in Reaxys

Rx-ID: 2884953 View in Reaxys 75/501 Yield

Conditions & References

65 %

With [Ru2(p-PriC6H4Me)2(μ-Cl)Cl]2 in tetrahydrofuran, Time= 15h, T= 40 °C Kita, Yasuyuki; Maeda, Hiroshi; Omori, Kana; Okuno, Takayuki; Tamura, Yasumitsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 23; (1993); p. 2999 - 3006 View in Reaxys

N N

E N

O N

Rx-ID: 24435120 View in Reaxys 76/501 Yield

Conditions & References 214 : EXAMPLE 214 EXAMPLE 214 Reaction of 4-(2-[1-(2-hydroxyethyl)-2-imidazolidinylideneamino]phenyl)morpholine (3 g prepared as described in Example 175) in dichloromethane (20 ml) with acetic anhydride (0.86 g) yielded 4-(2-[1-(2-acetyloxyethyl)-2-imidazolidinylideneamino]phenyl)morpholine (m.p. 89°-91° C.) which was recrystallized from hexane.

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in dichloromethane Patent; The Boots Company plc; US5223498; (1993); (A1) English View in Reaxys

N O

Rx-ID: 24664115 View in Reaxys 77/501 Yield

Conditions & References

75%

I : EXAMPLE I EXAMPLE I A solution of 135 ml. of acetic anhydride and 0.295 ml. of concentrated sulfuric acid was prepared. A 100 ml. three-necked-round-bottom-flask equipped with a magnetic stirrer, thermometer and an addition funnel, capped with a drying tube, was charged with 28 ml. of the acetic anhydride solution containing concentrated sulfuric acid. The reaction mixture was cooled to 0° C., and 25.4 ml. of ethyl acetoacetate was slowly added so as to maintain 0°-5° C. A new addition funnel was put in place and 9.8 ml. of 90percent nitric acid was added slowly so as to maintain the temperature between 0°-5° C. (Caution?--The reaction with nitric acid was violently exothermic.) After 90 minutes at a temperature of 0°-5° C., the reaction mixture was added to 200 ml. of ice cold ethanol and stirred for 10 minutes in an ice bath, and then overnight at room temperature. The ethanolic solution was treated with 0.31 gm. of anhydrous sodium carbonate and stirred for ten minutes The mixture was filtered, volatiles removed under vacuum, and finally distilled at 75° C./0.65 mm. to afford a 75percent yield of ethyl nitroacetate. Patent; W.R. Grace and Co.-Conn.; US5162572; (1992); (A1) English View in Reaxys

60%

IV : EXAMPLE IV EXAMPLE IV A solution of 100 ml. of acetic anhydride and 0.11 ml. of concentrated sulfuric acid was prepared. A 15 ml. two-necked-round-bottom-flask equipped with a magnetic stirrer, thermometer and an addition funnel, capped with a drying tube, was charged with 2.5 ml of the acetic anhydride solution containing concentrated sulfuric acid. The reaction mixture was cooled to a temperature between 15° to 20° C. and 2.54 ml. of ethyl acetoacetate was slowly added so as to maintain the temperature between 15° to 20° C. A new addition funnel was put in place and 1.2 ml. of 90percent nitric acid was added slowly so as to maintain temperature between 15° to 20° C. After 2 hours at 15° to 20° C., the reaction mixture was added to 20 ml. of ice cold ethanol and stirred for 10 minutes in an ice bath and then overnight at room temperature. The yield of ethyl nitroacetate was 60percent, as determined by gas chromatography, using naphthaline as an internal standard. Patent; W.R. Grace and Co.-Conn.; US5162572; (1992); (A1) English View in Reaxys

OH HO

Rx-ID: 24961839 View in Reaxys 78/501 Yield

Conditions & References 1 : Vinyl Acetate vs. 100 grams of para-hydroxybenzoic acid and 81 grams of potassium hydroxide were mixed into 400 mls of water in a stirred vessel. 80 mls of vinyl acetate was added and reacted at 28° C. for 2 hours. ACETIC ANHYDRIDE: With potassium hydroxide in water Patent; San Fu Chemical Co., Ltd.; US5136084; (1992); (A1) English View in Reaxys

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O O

Rx-ID: 1547129 View in Reaxys 79/501 Yield

Conditions & References

With ozone in polyethylene, Time= 3.5h, T= -75 °C Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

Rx-ID: 1547130 View in Reaxys 80/501 Yield

Conditions & References

60 % Spectr., 2 % Spectr., 15 % Spectr., 9 % Spectr.

With ozone in dichloromethane-d2, T= -78 °C , Title compound not separated from byproducts Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

O O

Rx-ID: 1547131 View in Reaxys 81/501 Yield

Conditions & References

58 % Spectr., 8 % Spectr., 1% Spectr., 6 % Spectr.

With ozone in polyethylene, Time= 4h, T= -75 °C , Further byproducts given Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

O O

Rx-ID: 1929127 View in Reaxys 82/501 Yield 21 % Spectr., 12 % Spectr., 5% Spectr., 48.3 % 62 % Spectr., 21 % Spectr., 12 % Spectr., 5 % Spectr.

Conditions & References With ozone in pentane, T= -75 °C Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

With ozone in pentane, T= -75 °C , Title compound not separated from byproducts Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

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O O

O racemate

racemate

Rx-ID: 2058328 View in Reaxys 83/501 Yield

Conditions & References

57 % Spectr., 33 % Spectr., 5% Spectr., 5 % Spectr. 57 % Spectr., 5 % Spectr., 5% Spectr., 33 % Spectr. 33 % Spectr., 5 % Spectr., 5% Spectr., 180 mg

With ozone in polyethylene, Time= 2h, T= -75 °C , Title compound not separated from byproducts Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

With ozone in polyethylene, Time= 2h, T= -75 °C Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

O O

Rx-ID: 2058329 View in Reaxys 84/501 Yield

Conditions & References With ozone, 1.) pentane, -75 deg C, 2.) 5 d, room temperature, Yield given. Multistep reaction. Yields of byproduct given Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys O

O O

Rx-ID: 2124617 View in Reaxys 85/501 Yield

Conditions & References With ozone, 1.) pentane, -75 deg C, 2.) room temperature, 8 d, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys With ozone, 1.) pentane, -75 deg C, 2.) room temperature, 8 d, Yield given. Multistep reaction. Yields of byproduct given Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

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O O E

Rx-ID: 2362048 View in Reaxys 86/501 Yield

Conditions & References With pyridine, osmium(VIII) oxide, 4-methylmorpholine N-oxide, 1) acetonitrile, water, room temp., 2) room temp., overnight, Yield given. Multistep reaction. Yields of byproduct given Yu; Simon; Tetrahedron; vol. 47; nb. 43; (1991); p. 9035 - 9052 View in Reaxys

O H

O O

Rx-ID: 2503748 View in Reaxys 87/501 Yield

Conditions & References

32 %, 28 in chloroform-d1, Time= 40h, T= 55 °C , Mechanism %, 2 %, 33 Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Journal of Organic Chemistry; vol. 56; nb. 12; (1991); p. %, 4 % 4005 - 4008 View in Reaxys 23 %, 8 %, in pentane, Time= 7.5h, T= -20 °C , Irradiation, Mechanism 3 %, 25 %, Griesbaum, Karl; Krieger-Beck, Petra; Beck, Johannes; Journal of Organic Chemistry; vol. 56; nb. 12; (1991); p. 4% 4005 - 4008 View in Reaxys

O O

Rx-ID: 2504718 View in Reaxys 88/501 Yield

Conditions & References

42 % Spectr., 10 % Spectr., 48 % Spectr.

With triphenylphosphine in chloroform-d1, Time= 2.5h, Title compound not separated from byproducts Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

O O

Rx-ID: 2504719 View in Reaxys 89/501 Yield 50 % Spectr., 48 % Spectr., 2% Spectr.

Conditions & References Time= 17h, T= 20 °C Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

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O O

Rx-ID: 2883107 View in Reaxys 90/501 Yield

Conditions & References T= 80 - 90 °C , Equilibrium constant Utkin, A. Yu.; Bogel'fer, L. Ya.; Chimishkyan, A. L.; Russian Journal of Physical Chemistry; vol. 65; nb. 7; (1991); p. 1049 - 1050; Zhurnal Fizicheskoi Khimii; vol. 65; (1991); p. 1974 - 1976 View in Reaxys

O O

Rx-ID: 3067117 View in Reaxys 91/501 Yield

O O

Rx-ID: 3354635 View in Reaxys 92/501 Yield

Conditions & References

12 % Spectr., 39 % Spectr., 22 % Spectr.

With ozone in pentane, T= -78 °C Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

39 % Spectr., 22 % Spectr., 12 % Spectr. O

With ozone in pentane, T= -78 °C Griesbaum, Karl; Greunig, Hans-Joachim; Volpp, Willi; Jung, In-Chan; Chemische Berichte; vol. 124; nb. 4; (1991); p. 947 - 956 View in Reaxys

Rx-ID: 24821333 View in Reaxys 93/501 Yield

Conditions & References 1 : EXAMPLE 1 EXAMPLE 1 The autoclave was charged with 17.5 g of methyl acetate (0.23 mol), 21 g of dimethyl acetal (0.23 mol), 1.3 mmoles of rhodium trichloride hydrate, 72 mmoles of lithium iodide, and 2.6 mmoles of triphenylphosphine. The reactor was heated to 180° C. and pressurized to 1,500 psig. Carbon monoxide was added, as indicated supra, as needed while the reaction proceeded for 40 minutes. The products were recovered as described above. Analysis of the products showed that 8 g of ethylidene diacetate, 6.1 g of methyl acetate and 14 g of acetic anhydride were produced during this short period of time. Patent; Union Carbide Chemicals and Plastics Technology Corporation; US5026903; (1991); (A1) English View in Reaxys 2 : EXAMPLE 2 EXAMPLE 2 The autoclave was charged with 17.5 g of methyl acetate (0.23 mol), 21 g of dimethyl acetal (0.23 mol), 1.5 mmoles of rhodium trichloride hydrate, 45 mmoles of lithium iodide and 6 mmoles of triphenylphosphine. The reactor was heated to 180° C. and pressurized to 1,500 psig.

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Carbon monoxide was added, as indicated supra, as needed while the reaction proceeded for 30 minutes. The products were recovered as described above. Analysis of the products showed that 5.8 g of ethylidene diacetate, 16.5 g of methyl acetate and 7 g of acetic anhydride were produced during this period of time. Patent; Union Carbide Chemicals and Plastics Technology Corporation; US5026903; (1991); (A1) English View in Reaxys

N H 2N NH

HCl

NH NH

Rx-ID: 24887924 View in Reaxys 94/501 Yield

Conditions & References

90%

8 : 6-[4-(Acetylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one EXAMPLE 8 6-[4-(Acetylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one [I; Ar 4-CH3 CONHC6 H4, R1 and R3 =H, R5 =CH3 ]was prepared from 1.73 g 6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one hydrochloride and 0.65 ml acetic anhydride according to the procedure of Example 7, and was obtained in 90percent yield as a colorless solid, m.p. above 300° C. when recrystallized from aqueous DMF. Patent; Sterling Drug Inc.; US4963561; (1990); (A1) English View in Reaxys

90%

8 : EXAMPLE 8 EXAMPLE 8 6-[4-(Acetylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one [I; Ar=4-CH3 CONHC6 H4, R1 and R3 =H, R5 =CH3 ] was prepared from 1.73 g 6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one hydrochloride and 0.65 ml acetic anhydride according to the procedure of Example 7, and was obtained in 90percent yield as a colorless solid, m.p. above 300° C. when recrystallized from aqueous DMF. Patent; Sterling Drug Inc.; US5010086; (1991); (A1) English View in Reaxys

(v5)

Tc O O(v3) (v3) OO (v3) O(v3) O O Tc O

(v6)

Rx-ID: 26739980 View in Reaxys 95/501 Yield

Conditions & References thermolysis of starting material at 400-460°C Kryuchkov, S. V.; German, K. E.; Simonov, A. E.; Sov. J. Coord. Chem. (Engl. Transl.); vol. 17; (1991); p. 255 261; Koordinatsionnaya Khimiya; vol. 17; (1991); p. 480 - 487 ; (from Gmelin) View in Reaxys

(v5)

Tc O O(v3) (v3) OO (v3) O(v3) O O Tc O

(v6)

Rx-ID: 26739993 View in Reaxys 96/501 Yield

Conditions & References thermolysis of starting material at 360-420°C Kryuchkov, S. V.; German, K. E.; Simonov, A. E.; Sov. J. Coord. Chem. (Engl. Transl.); vol. 17; (1991); p. 255 261; Koordinatsionnaya Khimiya; vol. 17; (1991); p. 480 - 487 ; (from Gmelin) View in Reaxys

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Cl (v6) Tc – O O(v3) (v3) OO (v3) O(v3) O O

K+

TcO

ClK

(v6)

Rx-ID: 26740876 View in Reaxys 97/501 Yield

Cl O

racemate

T-4

T-4 Cl O

Rx-ID: 1881984 View in Reaxys 98/501 Yield

Conditions & References With ozone, Time= 8h, T= -75 °C , ozonolysis on polyethylene, Product distribution Griesbaum, Karl; Greinert, Reinhard; Chemische Berichte; vol. 123; nb. 2; (1990); p. 391 - 397 View in Reaxys

O C

Rx-ID: 1922729 View in Reaxys 99/501 Yield

Conditions & References With ether-phosphane-silyloxy-rhodium, phosphane-silyloxy-platinum, Time= 5h, T= 130 °C , p= 37503Torr , var. times and temp.; other rhodium complexes, Product distribution, Mechanism Lindner, Ekkehard; Glaser, Erhard; Mayer, Hermann August; Wagner, Peter; Journal of Organometallic Chemistry; vol. 398; nb. 3; (1990); p. 325 - 337 View in Reaxys

O Si

O O

H H

Rx-ID: 2352763 View in Reaxys 100/501 Yield

Conditions & References

58 %, 26.9 %

With pyridine, Ambient temperature Daniewski, A. R.; Uskokovic, M. R.; Bulletin de la Societe Chimique de France; nb. 6; (1990); p. 849 - 856 View in Reaxys

(v5)

Rx-ID: 2885267 View in Reaxys 101/501 Yield 56.4 %

Conditions & References With phosphorus trichoride, Time= 2h, T= 45 - 50 °C

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Valitova, L. A.; Popova, E. V.; Ibragimov, Sh. N.; Ivanov, B. E.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 2.2; (1990); p. 366 - 370; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1990); p. 428 - 432 View in Reaxys 40.5 %, 8.7 %

With phosphorus trichoride, Time= 2h, T= 45 - 50 °C , other carboxylic acids, Product distribution Valitova, L. A.; Popova, E. V.; Ibragimov, Sh. N.; Ivanov, B. E.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 2.2; (1990); p. 366 - 370; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1990); p. 428 - 432 View in Reaxys

8.7 %, 40.5 %

With phosphorus trichoride, Time= 2h, T= 45 - 50 °C Valitova, L. A.; Popova, E. V.; Ibragimov, Sh. N.; Ivanov, B. E.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 2.2; (1990); p. 366 - 370; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1990); p. 428 - 432 View in Reaxys

O O O

Rx-ID: 1730601 View in Reaxys 102/501 Yield

Conditions & References

48 %

With oxygen, ozone, polyethylene, Time= 2h, T= -73 °C , ozonolyses on polyethylene (dry) and in pentane, Product distribution Griesbaum, Karl; Volpp, Willi; Huh, Tae-Seong; Jung, In Chan; Chemische Berichte; vol. 122; (1989); p. 941 944 View in Reaxys

48 %

With oxygen, ozone, polyethylene, Time= 2h, T= -73 °C , Yields of byproduct given Griesbaum, Karl; Volpp, Willi; Huh, Tae-Seong; Jung, In Chan; Chemische Berichte; vol. 122; (1989); p. 941 944 View in Reaxys

Rx-ID: 1861416 View in Reaxys 103/501 Yield

Conditions & References

18 %

With oxygen, ozone, polyethylene, Time= 6h, T= -73 °C , ozonolyses on polyethylene (dry) and in CDCl3, Product distribution Griesbaum, Karl; Volpp, Willi; Huh, Tae-Seong; Jung, In Chan; Chemische Berichte; vol. 122; (1989); p. 941 944 View in Reaxys

18 %

With oxygen, ozone, polyethylene, Time= 6h, T= -73 °C , Yields of byproduct given Griesbaum, Karl; Volpp, Willi; Huh, Tae-Seong; Jung, In Chan; Chemische Berichte; vol. 122; (1989); p. 941 944 View in Reaxys

O O

Rx-ID: 2653238 View in Reaxys 104/501 Yield

Conditions & References With triphenylphosphine in chloroform-d1, Time= 13h, T= -30 °C , Title compound not separated from byproducts

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Griesbaum, Karl; Volpp, Willi; Greinert, Reinhard; Greunig, Hans-Joachim; Schmid, Jurgen; Henke, Henning; Journal of Organic Chemistry; vol. 54; nb. 2; (1989); p. 383 - 389 View in Reaxys Br O

Rx-ID: 2909808 View in Reaxys 105/501 Yield

Conditions & References With n-butyllithium, water-d2, hexane, ether, Yield given. Multistep reaction Minabe, Masahiro; Cho, Bongsup P.; Harvey, Ronald G.; Journal of the American Chemical Society; vol. 111; nb. 11; (1989); p. 3809 - 3812 View in Reaxys

N N

O E

Rx-ID: 3253921 View in Reaxys 106/501 Yield

Conditions & References

88 % Spectr.

in benzene-d6, Time= 72h, T= 80 °C , thermolysis Majchrzak; Warkentin; Canadian Journal of Chemistry; vol. 67; nb. 11; (1989); p. 1753 - 1759 View in Reaxys

O O

Rx-ID: 3381738 View in Reaxys 107/501 Yield

Conditions & References

69 % Spectr., 17 % Spectr.

in benzene-d6, Time= 72h, T= 80 °C , thermolysis at different isomer ratio, Majchrzak; Warkentin; Canadian Journal of Chemistry; vol. 67; nb. 11; (1989); p. 1753 - 1759 View in Reaxys

Rx-ID: 25196155 View in Reaxys 108/501 Yield

Conditions & References 1 : 5-Acetylfuran-2-carboxylic Acid PREPARATION 1 5-Acetylfuran-2-carboxylic Acid A solution of 25.2 g. (0.2 mole) of methyl furan2-carboxylate in 75.6 ml. (0.8 mole) of acetic anhydride was prepared at -10° C., and then to this solution was added, dropwise, with stirring, at -10° C., 46.4 ml. (0.4 mole) of stannic chloride (SnCl4). The resulting mixture was allowed to warm to room temperature, and then stirring was continued at room temperature overnight. The reaction mixture was then cooled in an ice-bath, and 25 ml. of concentrated hydrochloric acid was added, with stirring. After 1 hour, the mixture was diluted with water and extracted with ethyl acetate. The extracts were washed with water, dried (Na2 SO4) and evaporated in vacuo. The residue, an oil, was purified by chromatography on silica gel, eluding with chloroform, to give 32 g. of methyl 5acetoacetylfuran-2-carboxylate as an orange solid, mp 89°-95° C.

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Patent; Reiter; Lawrence A.; US4814341; (1989); (A1) English View in Reaxys

O O

Rx-ID: 2166489 View in Reaxys 109/501 Yield

Conditions & References With pyridine, Time= 1.5h, T= 95 °C Maryanoff, Bruce E.; Reitz, Allen B.; Nortey, Samuel O.; Tetrahedron; vol. 44; nb. 11; (1988); p. 3093 - 3106 View in Reaxys

O N

Rx-ID: 2384477 View in Reaxys 110/501 Yield

Conditions & References in pyridine, Time= 72h, Ambient temperature, Yield given Guella; Mancini; Zibrowius; Pietra; Helvetica Chimica Acta; vol. 71; nb. 4; (1988); p. 773 - 782 View in Reaxys

racemate

Rx-ID: 2819702 View in Reaxys 111/501 Yield

Conditions & References

23 % Spectr., 23 % Spectr., 54 % Spectr.

in chloroform-d1, Time= 0.333333h, T= 10 °C , Product distribution Gollnick, Klaus; Koegler, Sigrid; Tetrahedron Letters; vol. 29; nb. 9; (1988); p. 1007 - 1010 View in Reaxys

O O

O H

O O

Rx-ID: 3009410 View in Reaxys 112/501 Yield 58 %

Conditions & References With pyridine, Time= 3.5h Maryanoff, Bruce E.; Reitz, Allen B.; Nortey, Samuel O.; Tetrahedron; vol. 44; nb. 11; (1988); p. 3093 - 3106

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View in Reaxys

O O

N O

racemate

Rx-ID: 3035703 View in Reaxys 113/501 Yield

Conditions & References

17 % Spectr., 41.5 % Spectr., 41.5 % Spectr.

in chloroform-d1, Time= 0.333333h, T= 0 °C , Product distribution Gollnick, Klaus; Koegler, Sigrid; Tetrahedron Letters; vol. 29; nb. 9; (1988); p. 1007 - 1010 View in Reaxys

Rx-ID: 3740857 View in Reaxys 114/501 Yield

Conditions & References With oxygen, T= 123 °C , p= 110259Torr , Mechanism, Product distribution, Rate constant Bogomol'nyi, G. M.; Freidin, B. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 61; nb. 11; (1988); p. 2597 2600,2377 - 2380 View in Reaxys

O O

NH 2

HCl O

O O H 2O

Rx-ID: 24982329 View in Reaxys 115/501 Yield

Conditions & References

2.36 g (90%)

1.E : N-t-Butyloxycarbonyl-p-Benzoyl-L-Phenylalanine (BOC-L-BPA) The solid was isolated by filtration (see below for filtrate processing), washed with water and a small amount of ethanol, and dried to give 2.36 g (90percent) of L-Bpa sesquihydrate (m.p. 178°-179°, αD 25 =3.0+-0.8°, concentration 1.01 g/100 ml of 1N HCl). Anal.: Calcd. for C16 H15 NO3.1.5 H2 O: C, 64.85; H, 6.12; N, 4.73. Found: C, 65.09; H, 6.08; N, 4.73. Reaction with acetic anhydride converted this material to the N-acetyl derivative (m.p. 187°-188°, αD 25 =+50.9+-0.8°, concentration 0.98 g/100 ml of ethanol). Anal.: Calcd. for C18 H17 NO4: C, 69.44; H, 5.50; n, 4.50. Found: C, 69.26; H, 5.58; N, 4.65. Patent; E. I. Du Pont de Nemours and Company; US4762881; (1988); (A1) English View in Reaxys

N EN

N O

Rx-ID: 24982330 View in Reaxys 116/501 Yield

Conditions & References 32.1 : (1) (1)

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1-Acetyl-6-(3,4-dimethoxyphenyl)-2,3-dimethyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.15 g) was obtained by reacting corresponding 1-unsubstituted compound (0.41 g) with acetic anhydride (2 ml). mp: 87°-89° C. IR (Nujol): 1690, 1630 cm-1. NMR (CDCl3, δ): 6.80 (4H, br s), 6.66 (1H, br s), 6.10 (1H, q, J=6 Hz), 5.41 (1H, s), 3.84 (3H, s), 3.79 (3H, s), 3.09 (3H, s), 2.23 (3H, s), 2.00 (6H, s), 1.70 (3H, s), 1.39 (3H, d, J=6 Hz). Patent; Fujisawa Pharmaceutical Co., Ltd.; US4725600; (1988); (A1) English View in Reaxys

(v3)

O O O O U – O (v3)

NH 2 (v3)

(v10)

O2U

H+

Rx-ID: 26413766 View in Reaxys 117/501 Yield

Conditions & References in neat (no solvent), byproducts: CO, CO2, H2O; thermal decompn. of uranyl compd.; detected IR spect. Seisenbaeva, G. A.; Santalova, N. A.; Dunaeva, K. M.; Sov. J. Coord. Chem. (Engl. Transl.); vol. 14; (1988); p. 682 - 685; Koordinatsionnaya Khimiya; (1988); p. 1214 - 1218 ; (from Gmelin) View in Reaxys H N

racemate O

Rx-ID: 2883538 View in Reaxys 118/501 Yield

Conditions & References in water, T= 25 °C , at pH 5, Rate constant Somayaji, V.; Brown, R. S.; Journal of the American Chemical Society; vol. 109; nb. 15; (1987); p. 4738 - 4739 View in Reaxys

3-(5-ethyl-1,2,4-oxadiazol-3-yl)-8-methyl-5,6-methyl-6-oxo-4Himidazo(1,5-a)(1,4)benzodiazepine

Rx-ID: 24981785 View in Reaxys 119/501 Yield

Conditions & References 2.D : 3-(5-ethyl-1,2,4-oxadiazol-3-yl)-8-methyl-5,6-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine D. 3-(5-ethyl-1,2,4-oxadiazol-3-yl)-8-methyl-5,6-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine A mixture of 450 mg of the product of C and 15 ml propionic anhydride was stirred at 100° C. for 10 min. Then 25 ml of dry ethanol, 3 g molecular sieves (3 Å) and 50 mg of sodium was added and the resulting mixture was refluxed for 4 hours. The mixture was then filtered and the filtrate was reduced to 10 ml. Then 70 ml of water was added whereupon the title compound precipitated. The precipitate was washed with water and petroleum ether. Yield 150 mg. M.p. 174.6°-176.4° C. In the same manner by reaction with acetic anhydride the following compounds are synthesised. 3-(3-(5-methyl-1,2,4-oxadiazol3-yl)-8-methyl-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine M.p. 276° C. dec. Patent; A/S Ferrosan; US4670433; (1987); (A1) English View in Reaxys

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N-(2-carboxyethyl)-diphenimide Rx-ID: 24982328 View in Reaxys 120/501 Yield

Conditions & References

17%

5 : Preparation of N-(2-Carboxyethyl)-Diphenimide (Compound No. 17) EXAMPLE 5 Preparation of N-(2-Carboxyethyl)-Diphenimide (Compound No. 17) A mixture of diphenic anhydride (7.0 g, 0.03 mol), beta- alanine (2.7 g, 0.03 mol) and DMF(60 ml) was stirred under reflux for six hours. The solvent was removed in vacuo, and the resulting residue dissolved in a acetic anhydride (50 ml) and glacial acetic acid (10 ml). The solution was stirred under reflux for two hours after which the volatile material was removed in vacuo. The residue was recrystallized from isopropanol to produce the acid product, N-(2-carboxyethyl)-diphenimide. The product was found to have a melting point of 169°-171° C. It was obtained in a yield of 17percent. Analysis: Calculated for C17 H13 NO4: C, 69.15; H, 4.44; N, 4.74. Found: C, 68.95; H, 4.50; N, 4.69. 1

H-NMR (δ,TMS): 7.50-7.88 (m, 8H, aromatic)

Patent; Research Corporation; US4689326; (1987); (A1) English View in Reaxys F

F F

Rx-ID: 24982331 View in Reaxys 121/501 Yield

Conditions & References

90 %

3 : Step (2) EXAMPLE 3 Step (2) utilizing acetic anhydride as the acetylating agent To a mixture of 2.43 moles (324 g.) of aluminum chloride in 648 ml. of dichloromethane is added a solution of 0.88 mole (274 g.) of 1,4-bis(2,2,2-trifluoroethoxy)benzene and 0.97 mole (92 ml.) of acetic anhydride in 880 ml. of dichloromethane over a 3 hour period while maintaining the temperature at above 0° C. The reaction mixture is then heated to its reflux temperature and stirred at reflux for 5 hours. The progress of the reaction is followed using thin-layer chromatography. The reaction mixture is placed in an ice bath and ice and 10 percent hydrochloric acid are added slowly to decompose the aluminum chloride complex. The temperature of the reaction mixture is not allowed to exceed 25° C. The organic phase is separated and washed once with 2 liters of 10 percent hydrochloric acid and then with 2 liters of water. The combined aqueous phase is extracted with several liters of dichloromethane. The organic phase is dried over magnesium sulfate, then evaporated to provide a moist residue. Hexane is added to the residue and the resulting solid is collected by filtration and washed with hexane. Upon drying, 250 g. of light yellow crystalline 2,5-bis(2,2,2-trifluoroethoxy)acetophenone is obtained. The yield is 90 percent, the m.p. is 84° to 86° C. Patent; Riker Laboratories, Inc.; US4642384; (1987); (A1) English View in Reaxys

O O

P O

O O

O O P

P O

Rx-ID: 244939 View in Reaxys 122/501 Yield

Conditions & References Erhitzen im Vakuum

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Petrow; Neimyschewa; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 1822,1824;engl.Ausg.S.1793,1795 View in Reaxys Ambient temperature, 6 months, Product distribution Symes, Jill; Modro, Tomasz A.; Canadian Journal of Chemistry; vol. 64; (1986); p. 1702 - 1708 View in Reaxys

Rx-ID: 1973518 View in Reaxys 123/501 Yield

Conditions & References With polyetylene, ozone, triphenylphosphine, 1) -75 deg C, Multistep reaction Griesbaum, Karl; Volpp, Willi; Angewandte Chemie; vol. 98; nb. 1; (1986); p. 108 - 109 View in Reaxys

O O

Rx-ID: 2710392 View in Reaxys 124/501 Yield

Conditions & References With P4-VP in dichloromethane, Time= 1h, T= 0 °C , Yield given. Yields of byproduct given Fife, Wilmer K.; Zhang, Zhi-dong; Tetrahedron Letters; vol. 27; nb. 41; (1986); p. 4933 - 4936 View in Reaxys

O O

Rx-ID: 3321418 View in Reaxys 125/501 Yield

Conditions & References With P4-VP in dichloromethane, Time= 0.25h, T= 0 °C , Yield given. Yields of byproduct given Fife, Wilmer K.; Zhang, Zhi-dong; Tetrahedron Letters; vol. 27; nb. 41; (1986); p. 4933 - 4936 View in Reaxys O O O

Rx-ID: 24903715 View in Reaxys 126/501 Yield

Conditions & References 3 : EXAMPLE 3 EXAMPLE 3 4.80 g (17.1 mmol) of thioxanthone-3,4-dicarboxylic acid imide are refluxed in 511 ml of 0.1N NaOH solution for 90 minutes. The resulting mixture of amide acid and dicarboxylic acid sodium salts is acidified with concentrated hydrochloric acid and refluxed for 18 hours. The crude thioxanthone-3,4-dicarboxylic acid is filtered off, washed with water and converted into anhydride by refluxing in xylene with 11 ml of acetic anhydride, and the anhydride is precipitated after partial evaporation of the solution. 4.32 g (90percent of theory) of thioxanthone-3,4-dicarboxylic acid anhydride are obtained; melting point: 330°-301° C. Analysis for C15 H6 O4 S (molecular weight: 282.27): calculated: C 63.83, H 2.14, O 22.67, S 11.36percent, found: C 63.97, H 2.01, O 22.61, S 11.13percent.

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Patent; Ciba-Geigy Corporation; US4585876; (1986); (A1) English View in Reaxys

F Cl

–O

O Na +

O F

S S

Rx-ID: 1783390 View in Reaxys 127/501 Yield

Conditions & References

52 %

Time= 12h, T= 0 °C Haas,A.; Lieb,M.; Zhang,Y.; Journal of Fluorine Chemistry; vol. 29; (1985); p. 297 View in Reaxys

O C

Rx-ID: 1922756 View in Reaxys 128/501 Yield

Conditions & References

68.1 %, 5.3 %

5.3 %, 68.1 %

With tributylphosphine, hydrogen, methyl iodide, [rhodium(I)(carbonyl)2(acetylacetonate)], palladium diacetate in acetic acid, Time= 4h, T= 160 °C , p= 147102Torr Kudo, Kiyoshi; Mori, Sadayuki; Sugita, Nobuyuki; Chemistry Letters; (1985); p. 265 - 268 View in Reaxys With tributylphosphine, hydrogen, methyl iodide, [rhodium(I)(carbonyl)2(acetylacetonate)], palladium diacetate in acetic acid, Time= 4h, T= 160 °C , p= 152000Torr , The effect of mixed transition metal catalysts and the effect of various bases was investigated., Product distribution Kudo, Kiyoshi; Mori, Sadayuki; Sugita, Nobuyuki; Chemistry Letters; (1985); p. 265 - 268 View in Reaxys

O C

Rx-ID: 1922763 View in Reaxys 129/501 Yield

Conditions & References

4.5 %, 6.6 %, 0.8 %, 1.3 %

With methyl iodide, carbon, molybdenum, T= 250 °C , p= 11400Torr , investigation on effect of carrier materials with different catalysts and effect of pressure, Product distribution Shikada, Tsutomu; Yagita, Hiroshi; Fujimoto, Kaoru; Tominaga, Hiro-o; Chemistry Letters; (1985); p. 547 - 550 View in Reaxys

NH N

H 2N N

O P

Rx-ID: 2883266 View in Reaxys 130/501 Yield 89 %, 51 %

Conditions & References in diethyl ether, Time= 3h, Ambient temperature Kozlov, E. S.; Dubenko, L. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 12; (1985); p. 2692 - 2696,2393 2396 View in Reaxys

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O C

Rx-ID: 3885777 View in Reaxys 131/501 Yield

Conditions & References With zinc diacetate, hydrogen, Rhodium trichloride, Time= 2h, T= 200 °C , p= 76000Torr , Yield given. Further byproducts given. Yields of byproduct given Mamyan, V. A.; Sominskii, S. D.; Pirozhkov, S. D.; Barsegyan, V. L.; Vardanyan, V. D.; Lapidus, A. L.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; nb. 10; (1985); p. 2095 - 2098; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1985); p. 2265 - 2268 View in Reaxys With Rhodium trichloride, zinc diacetate, hydrogen, Time= 2h, T= 200 °C , p= 76000Torr , various molar ratio of CO:H2, metal halides, temperature and content of MeI, Product distribution, Mechanism Mamyan, V. A.; Sominskii, S. D.; Pirozhkov, S. D.; Barsegyan, V. L.; Vardanyan, V. D.; Lapidus, A. L.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; nb. 10; (1985); p. 2095 - 2098; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1985); p. 2265 - 2268 View in Reaxys

Co2 (CO)8

S O

Rx-ID: 25199187 View in Reaxys 132/501 Yield

Conditions & References 1 : Preparation of acetic anhydride and EDA: hydrogen present EXAMPLE 1 Preparation of acetic anhydride and EDA: hydrogen present Methyl acetate (35 g), acetic acid (15 g), methyl p-toluenesulphonate (10 g), Co2 (CO)8 (0.2 g), N-methylimidazole (2.3 g) and sodium iodide (0.5 g), iodide:cobalt atomic ratio 3:1 were charged to a stainless steel autoclave which was pressured to 100 psig H2 and to a further 1020 psig with CO at room temperature. This vessel was then heated and stirred for one hour at 130° C. At this temperature the initial total pressure was approximately 1300 psig. Gas Chromatographic (G.C.) analysis of the reaction mixture showed it to contain 0.6 g of acetic anhydride and 1.0 g of ethylidene diacetate. With 1-methyl-1H-imidazole, H2, sodium iodide, acetic anhydride, acetic acid in methyl acetate Patent; BP Chemicals Limited; US4534912; (1985); (A1) English View in Reaxys

Rx-ID: 1929409 View in Reaxys 133/501 Yield

Conditions & References With D2SO4 (sulfonic acid-d2), T= 32.5 °C , Rate constant, Mechanism Montheard, Jean-Pierre; Camps, Marcel; Chatzopoulos, Michel; Benzaid, Ahmed; Bulletin de la Societe Chimique de France; vol. 2; nb. 3-4; (1984); p. 109 - 116 View in Reaxys O

racemate

Rx-ID: 2359107 View in Reaxys 134/501

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Yield

Conditions & References in pyridine, Time= 48h, Ambient temperature, Yield given. Title compound not separated from byproducts Heathcock, Clayton H.; Kiyooka, Syun-ichi; Blumenkopf, Todd A.; Journal of Organic Chemistry; vol. 49; nb. 22; (1984); p. 4214 - 4223 View in Reaxys

Rx-ID: 2880707 View in Reaxys 135/501 Yield

Conditions & References With sulfuric acid, T= 32.5 °C , Title compound not separated from byproducts Montheard, Jean-Pierre; Camps, Marcel; Chatzopoulos, Michel; Benzaid, Ahmed; Bulletin de la Societe Chimique de France; vol. 2; nb. 3-4; (1984); p. 109 - 116 View in Reaxys With perchloric acid, T= 40 °C , Rate constant Montheard; Camps; Ait-Yahia; Guilluy; Tetrahedron; vol. 36; nb. 20-21; (1980); p. 2967 - 2975 View in Reaxys With methanesulfonic acid, k2, Rate constant Montheard, Jean-Pierre; Camps, Marcel; Benzaid, Ahmed; Chemistry Letters; (1981); p. 523 - 526 View in Reaxys With sulfuric acid, k2, Rate constant Montheard, Jean-Pierre; Camps, Marcel; Benzaid, Ahmed; Chemistry Letters; (1981); p. 523 - 526 View in Reaxys With BF3·2HOAc, k2, Rate constant Montheard, Jean-Pierre; Camps, Marcel; Benzaid, Ahmed; Chemistry Letters; (1981); p. 523 - 526 View in Reaxys With sulfuric acid, T= 32.5 °C , further enolic esters, isotope effect, Rate constant, Mechanism Montheard, Jean-Pierre; Camps, Marcel; Chatzopoulos, Michel; Benzaid, Ahmed; Bulletin de la Societe Chimique de France; vol. 2; nb. 3-4; (1984); p. 109 - 116 View in Reaxys

N O

Rx-ID: 2885266 View in Reaxys 136/501 Yield

Conditions & References With 4-Methyl-N-(2,2-diphenylethenylidene)aniline in acetonitrile, T= 30 °C , in the presence of pyridine, Rate constant, Product distribution Akhrem, A. A.; Lakhvich, F. A.; Pyrko, A. N.; Lis, L. G.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 2335 - 2339; Zhurnal Organicheskoi Khimii; vol. 20; nb. 12; (1984); p. 2565 - 2570 View in Reaxys

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O –O

N+

Rx-ID: 3174123 View in Reaxys 137/501 Yield

Conditions & References With sodium perchlorate, acetic anhydride, Equilibrium constant Schmidt, Cornelia; Pragst, Fritz; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 24; nb. 9; (1984); p. 332 - 333 View in Reaxys

O–

Rx-ID: 3316399 View in Reaxys 138/501 Yield

Conditions & References in 1,4-dioxane, water, T= 22 °C , pH=4.63, Rate constant Palling, David J.; Jencks, William P.; Journal of the American Chemical Society; vol. 106; nb. 17; (1984); p. 4869 4876 View in Reaxys O

N O

Rx-ID: 3353387 View in Reaxys 139/501 Yield

Conditions & References Yield given. Multistep reaction Baldwin; Chan; Gallacher; Otsuka; Tetrahedron; vol. 40; nb. 21; (1984); p. 4513 - 4525 View in Reaxys

O S P

S S

Rx-ID: 3576364 View in Reaxys 140/501 Yield

Conditions & References Ambient temperature, thermal stability; further temperature Hennig, Heinz-Werner; Sartori, Peter; Steinbrecht, Ulrich; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 39; nb. 3; (1984); p. 284 - 289 View in Reaxys

O O

Rx-ID: 1853266 View in Reaxys 141/501 Yield 82 %, 69 %

Conditions & References Kostin, V. P.; Sinyashin, O. G.; Batyeva, E. S.; Pudovik, A. N.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 7; (1982); p. 1494; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1982); p. 1673 - 1674 View in Reaxys T= 25 °C , various time, with or without acetic acid or pyridine, Product distribution

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Sinyashin, O. G.; Kostin, V. P.; Batyeva, E. S.; Pudovik, A. N.; Ivasyuk N. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1706 - 1713,1535 - 1541 View in Reaxys O O

Rx-ID: 1890705 View in Reaxys 142/501 Yield

Conditions & References

17.3 % With triethylamine in acetonitrile, Ambient temperature, electrolysis, Mechanism, Product distribution Turnov., 54 % Turnov. Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys 54 % Turn- With triethylamine in acetonitrile, Ambient temperature, electrolysis ov., 17.3 % Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; Turnov. (1983); p. 375 - 388 View in Reaxys O

O C

Rx-ID: 1922760 View in Reaxys 143/501 Yield

Conditions & References

20.5 %, 17.5 %, 2.1 %

With methyl iodide promoter, nickel, carbon, T= 250 °C , p= 31160Torr , other reaction pressure, time factor, reagents mol ratio, other partial pressure of methyl iodide promoter, Product distribution Fujimoto, Kaoru; Shikada, Tsutomu; Miyauchi, Michiharu; Tominaga, Hiro-o; Chemistry Letters; (1983); p. 1157 - 1160 View in Reaxys

Rx-ID: 1933047 View in Reaxys 144/501 Yield

Conditions & References With air, T= 160 °C , p= 10500.8Torr , Other temperature, Product distribution, Mechanism Bogomol'nyi, G. M.; Mirantsova, N. A.; Pintegova, N. N.; Freidin, B. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 56; nb. 2; (1983); p. 627 - 631,598 - 601 View in Reaxys

O O

Rx-ID: 1953844 View in Reaxys 145/501 Yield 47 %, 4.7 %, 86.8 %

Conditions & References With triethylamine in acetonitrile, Ambient temperature, electrolysis, Further byproducts given Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys

47 %, 86.8 %, 4.7 %

With triethylamine in acetonitrile, Ambient temperature, electrolysis, Further byproducts given Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys

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HO O

Rx-ID: 2107450 View in Reaxys 146/501 Yield

Conditions & References

49 % Turn- With triethylamine in acetonitrile, Ambient temperature, electrolysis ov., 11 % Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; Turnov. (1983); p. 375 - 388 View in Reaxys 49 % Turn- With triethylamine in acetonitrile, Ambient temperature, electrolysis, Mechanism, Product distribution ov., 11 % Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; Turnov. (1983); p. 375 - 388 View in Reaxys

O OH

Rx-ID: 2165810 View in Reaxys 147/501 Yield

Conditions & References

93 %

With triethylamine in acetonitrile, Ambient temperature, electrolysis Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys

93 %

With triethylamine in acetonitrile, Ambient temperature, electrolysis, Product distribution Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys

O O

Rx-ID: 2186288 View in Reaxys 148/501 Yield

Conditions & References

93 % Turn- in acetonitrile, Ambient temperature, electrolysis, Product distribution ov. Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys O

Rx-ID: 2899762 View in Reaxys 149/501 Yield

Conditions & References With air, T= 120 °C , p= 10500.8Torr , Other temperature, Product distribution, Mechanism Bogomol'nyi, G. M.; Mirantsova, N. A.; Pintegova, N. N.; Freidin, B. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 56; nb. 2; (1983); p. 627 - 631,598 - 601 View in Reaxys

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Rx-ID: 3229696 View in Reaxys 150/501 Yield

Conditions & References

89 %, 72 %

With acetyl chloride, Time= 0.5h, Ambient temperature Sinyashin, O. G.; Kostin, V. P.; Batyeva, E. S.; Pudovik, A. N.; Ivasyuk N. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1706 - 1713,1535 - 1541 View in Reaxys

Rx-ID: 3310186 View in Reaxys 151/501 Yield

Conditions & References

86.8 %, 4.7 %, 47 %

in acetonitrile, Ambient temperature, electrolysis, Further byproducts given Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys

Rx-ID: 3310187 View in Reaxys 152/501 Yield

Conditions & References

86.8 % Turnov., 47 % Turnov., 4.7 % Turnov.

in acetonitrile, Ambient temperature, electrolysis, Mechanism, Product distribution Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys

O S

Rx-ID: 3321632 View in Reaxys 153/501 Yield

Conditions & References T= 25 °C , various time, with or without acetic acid or pyridine, Product distribution Sinyashin, O. G.; Kostin, V. P.; Batyeva, E. S.; Pudovik, A. N.; Ivasyuk N. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1706 - 1713,1535 - 1541 View in Reaxys

P S

O S

O O

Rx-ID: 3600981 View in Reaxys 154/501 Yield 56 %

Conditions & References With benzoyl chloride, Time= 1h, Ambient temperature Sinyashin, O. G.; Kostin, V. P.; Batyeva, E. S.; Pudovik, A. N.; Ivasyuk N. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1706 - 1713,1535 - 1541 View in Reaxys

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O O

Rx-ID: 3600982 View in Reaxys 155/501 Yield

Conditions & References

82 %, 69 %

With acetyl-bromide, Time= 1h, Ambient temperature Sinyashin, O. G.; Kostin, V. P.; Batyeva, E. S.; Pudovik, A. N.; Ivasyuk N. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1706 - 1713,1535 - 1541 View in Reaxys

Cl Cl

Cl O

O Cl

Rx-ID: 3600983 View in Reaxys 156/501 Yield

Conditions & References

50 %

With 2,2,2-trichloroacetyl chloride, Time= 1h, Ambient temperature Sinyashin, O. G.; Kostin, V. P.; Batyeva, E. S.; Pudovik, A. N.; Ivasyuk N. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1706 - 1713,1535 - 1541 View in Reaxys O

O O

O N

O O

Rx-ID: 3737591 View in Reaxys 157/501 Yield

Conditions & References

70 %, 4.2 %, 4.8 %, 5.5 %

–O

With triethylamine, Ambient temperature, electrolysis, Mechanism, Product distribution Thomas, Hans G.; Gabriel, Juergen; Fleischhauer, Joerg; Raabe, Gerhard; Chemische Berichte; vol. 116; nb. 1; (1983); p. 375 - 388 View in Reaxys O

K+

SO2, K2COOSO3

Rx-ID: 8287112 View in Reaxys 158/501 Yield

Conditions & References With sulfuryl dichloride, Time= 0.15h, T= 150 °C , Product distribution Nakamura, Shigeaki; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 1 - 4 View in Reaxys

–O

SO2

Li+

Rx-ID: 8287148 View in Reaxys 159/501 Yield

Conditions & References With sulfuryl dichloride, Time= 0.433333h, T= 150 °C , Product distribution

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Nakamura, Shigeaki; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 1 - 4 View in Reaxys –O

SO2

Na +

Rx-ID: 8287149 View in Reaxys 160/501 Yield

Conditions & References With sulfuryl dichloride, Time= 0.7h, T= 150 °C , Product distribution Nakamura, Shigeaki; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 1 - 4 View in Reaxys

–O

SO2

Li+

Rx-ID: 8287157 View in Reaxys 161/501 Yield

Conditions & References With sulfuryl dichloride, Time= 5.83333h, T= 18 - 31 °C , Product distribution Nakamura, Shigeaki; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 1 - 4 View in Reaxys

–O

SO2

K+

Rx-ID: 8287158 View in Reaxys 162/501 Yield

Conditions & References With sulfuryl dichloride, Time= 0.333333h, T= 18 - 31 °C , Product distribution Nakamura, Shigeaki; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 1 - 4 View in Reaxys

–O

SO2

Na +

Rx-ID: 8287159 View in Reaxys 163/501 Yield

Conditions & References With sulfuryl dichloride, Time= 0.5h, T= 18 - 31 °C , Product distribution Nakamura, Shigeaki; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 1 - 4 View in Reaxys

O 2

O– Pd2+

O Pd

Rx-ID: 26951059 View in Reaxys 164/501 Yield

Conditions & References With carbon monoxide, sodium acetate in acetic acid, Kinetics, at 60°C; moniored by UV Stromnova, T. A.; Vargaftik, M. N.; Moiseev, I. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 32; (1983); p. 21 - 24; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 32; (1983); p. 31 - 34 ; (from Gmelin) View in Reaxys

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O O

Rx-ID: 1525826 View in Reaxys 165/501 Yield

Conditions & References T= 800 °C , p= 1.4Torr , without methanol, other 1,3-dioxol-2-ones, Mechanism, Product distribution Breitbeil, Fred W.; Skrobot, Angeline A.; Journal of Organic Chemistry; vol. 47; nb. 4; (1982); p. 702 - 704 View in Reaxys

O O

Rx-ID: 1915270 View in Reaxys 166/501 Yield

Conditions & References in methanol, T= -12 °C , Synthesis of Pb-organic compounds; other Ph(n)Pb(OAc)(4-n) Huber, Friedo; Schillings, Karl-Ludwig; Journal of Fluorine Chemistry; vol. 19; (1982); p. 521 - 528 View in Reaxys O S

O O

Rx-ID: 2017554 View in Reaxys 167/501 Yield

Conditions & References

76 %, 19 %, 5 %

With oxygen, T= -78 - 25 °C , TPP as sensitizer, Product distribution, Mechanism Ando, Wataru; Miyazaki, Hajime; Ito, Kenji; Auchi, Daikan; Tetrahedron Letters; vol. 23; nb. 5; (1982); p. 555 556 View in Reaxys

Rx-ID: 2062829 View in Reaxys 168/501 Yield

Conditions & References With sulfuric acid, T= 25 °C , Kinetics, Mechanism Montheard, Jean-Pierre; Camps, Marcel; Benzaid, Ahmed; Pascal, Jean-Louis; Tetrahedron Letters; vol. 23; nb. 34; (1982); p. 3483 - 3486 View in Reaxys T= 32.5 °C , var. cat.: CH3SO3H, BF3, Rate constant Montheard, J. P.; Camps, M.; Benzaid, A.; Bulletin de la Societe Chimique de France; vol. 1; nb. 1-2; (1981); p. 33 - 41 View in Reaxys

N N

O O

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Cl O

Rx-ID: 2842707 View in Reaxys 169/501 Yield

Conditions & References

50 % Spectr., 72 % Spectr., 9% Spectr., 20 % Spectr., 20 % Spectr. S

With tetrachloromethane, Time= 72h, T= 79.5 °C , other oxadiazoline, Rate constant, Mechanism, Product distribution Bekhazi, Michel; Warkentin, John; Journal of Organic Chemistry; vol. 47; nb. 25; (1982); p. 4870 - 4873 View in Reaxys

Rx-ID: 3320776 View in Reaxys 170/501 Yield

Conditions & References

89 %, 72 %

Time= 0.5h, T= 20 °C Kostin, V. P.; Sinyashin, O. G.; Batyeva, E. S.; Pudovik, A. N.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 7; (1982); p. 1494; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1982); p. 1673 - 1674 View in Reaxys

Br–

S+

Rx-ID: 3982052 View in Reaxys 171/501 Yield

Conditions & References in dichloromethane, T= -8 °C , further temperature, also with SbCl5; half-life time, Product distribution Goetz-Grandmont, Genevieve J.; Leroy, Maurice J.F.; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1747 - 1765 View in Reaxys

N2, N2O Rx-ID: 8427208 View in Reaxys 172/501

Yield

Conditions & References

55 %, 27 %, 6 %

With oxygen in dichloromethane, T= -78 °C , Irradiation, TPP as sensitizer, Product distribution, Mechanism Ando, Wataru; Miyazaki, Hajime; Ito, Kenji; Auchi, Daikan; Tetrahedron Letters; vol. 23; nb. 5; (1982); p. 555 556 View in Reaxys

estra-1,3,5(10)-triene-3-benzoyloxy-17β-oxycarbonylmethyl-16,16dimethyl-11α,15α-diacetoxy-9-oxo-2(trans)-13(trans)-prostadinoate

Rx-ID: 25059818 View in Reaxys 173/501 Yield

Conditions & References 6 : Preparation of estra-1,3,5(10)-triene-3-benzoyloxy-17β-oxycarbonylmethyl-16,16-dimethyl-11α,15α-dihydroxy-9-oxo-2(trans)-13(trans)-prostadienoate ((Me)2 --PGE2 '--E--BA) 25 Milligram of the resulting (Me)2 --PGE2 '--E--BA was dissolved into 1.0 ml. of anhydrous pyridine and 0.20 mg. of acetic anhydride was added and the reaction was carried out for 4 hours by cooling with ice.

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Then, the solvent was distilled off at 40° C. under a reduced pressure. The residue was chromatographed on a silica gel with a mixed solvent (ethyl acetate: cyclohexane at ratio of 50:50 by volume) to obtain 20 mg. of oily estra-1,3,5(10)-triene-3-benzoyloxy-17β-oxycarbonylmethyl-16,16-dimethyl-11α, 15α-diacetoxy-9-oxo-2(trans)-13(trans)-prostadinoate ((Me)2 --PGE2 '--E--2AC--BA). The product was confirmed by the elementary analysis and IR spectrum (cm-1). Elementary analysis: IR spectrum: (cm-1) 2950, 2920, 2850, 1735, 1705, 1585, 1490, 1448, 1415, 1381, 1368, 1350, 1235, 1143, 1090, 1020, 970, 890, 780, 720, 698, 683 Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US4318908; (1982); (A1) English View in Reaxys O

estra-1,3,5(10)-triene-3-benzoyloxy-17β-oxycarbonylmethyl-16,16dimethyl-11α,15α-diacetoxy-9-oxo-5(cis)-13(trans)-prostadinoate

Rx-ID: 25059819 View in Reaxys 174/501 Yield

Conditions & References 2 : Preparation of estra-1,3,5(10)-triene-3-benzoyloxy-17β-oxycarbonylmethyl-16,16-dimethyl-11α,15α-dihydroxy-9-oxo-5(cis)-13(trans)-prostadienoate ((Me)2 --PGE2 --E--BA) 26 Milligram of the resulting (Me)2 --PGE2 --E--BA was dissolved into 0.9 ml. of anhydrous pyridine and 0.17 mg. of acetic anhydride was added and the reaction was carried out for 4 hours by cooling with ice. Then, the solvent was distilled off at 40° C. under a reduced pressure. The residue was chromatographed on a silica gel with a mixed solvent (ethyl acetate: cyclohexane at ratio of 50:50 by volume) to obtain 22 mg. of oily estra-1,3,5(10)-triene-3-benzoyloxy-17β-oxycarbonylmethyl-16,16-dimethyl-11α, 15α-diacetoxy-9-oxo-5(cis)-13(trans)-prostadinoate ((Me)2 --PGE2 --E--2AC--BA). The product was confirmed by the elementary analysis and IR spectrum (cm-1). Elementary analysis: IR spectrum: (cm-1) 2950, 2920, 2850, 1735, 1705, 1585, 1490, 1448, 1415, 1381, 1368, 1350, 1235, 1143, 1090, 1020, 970, 890, 780, 720, 698, 683 Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US4318908; (1982); (A1) English View in Reaxys

Re2 (CO)10

N+

CH3 I

I–

Rx-ID: 25122845 View in Reaxys 175/501 Yield

Conditions & References 4 : EXAMPLE 4 EXAMPLE 4 250 g methyl acetate, 1.6 g RhCl3.3H 2 O, 3.9 g Re2 (CO)10, 50 g CH3 I, 25 g acetic acid and 68 g N,N-dimethylimidazolium iodide were placed in a Hastelloy autoclave and reacted therein under a total pressure of 100 bars at 435° K. with a mixture of 60 volume percent CO and 40 volume percent H2. After a reaction period of 17 minutes, 145 g of a mixture of 60.9 mass percent, 1,1-diacetoxyethane and 39.1 mass percent acetic anhydride was obtained from the reaction product. With H2, CO, acetic acid in methyl acetate Patent; Hoechst Aktiengesellschaft; US4319038; (1982); (A1) English View in Reaxys

CH3 I

N+

I–

Rx-ID: 25122846 View in Reaxys 176/501 Yield

Conditions & References 1 : (Outside invention) EXAMPLE 1 (Outside invention)

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250 g methyl acetate, 1.6 g RhCl3.3H 2 O, 50 g CH3 I, 25 g acetic acid and 68 g N,N-dimethylimidazolium iodide were placed in a Hastelloy autoclave and reacted therein under total pressure of 100 bars at 435° K. with a mixture of 60 volume percent CO and 40 volume percent H2. After a reaction period of 23 minutes, 109 g of a mixture of 60 mass percent 1,1-diacetoxyethane and 40 mass percent acetic anhydride was obtained from the reaction mixture. With H2, CO, acetic acid in methyl acetate Patent; Hoechst Aktiengesellschaft; US4319038; (1982); (A1) English View in Reaxys 2 : (Outside invention) EXAMPLE 2 (Outside invention) 250 g methyl acetate, 1.6 g RhCl3.3H 2 O, 5.4 g Cr(CO)6, 50 g CH3 I, 25 g acetic acid and 68 g N,N-dimethylimidazolium iodide were placed in a Hastelloy autoclave and reacted therein under a total pressure of 100 bars at 435° K. with a mixture of 60 volume percent CO and 40 volume percent H2. After a reaction period of 20 minutes, 146 g of a mixture of 37.7 mass percent, 1,1-diacetoxyethane and 62.3 mass percent acetic anhydride was obtained from the reaction mixture. With H2, CO, acetic acid, Cr(CO)6 in methyl acetate Patent; Hoechst Aktiengesellschaft; US4319038; (1982); (A1) English View in Reaxys O

O O

Rx-ID: 351643 View in Reaxys 177/501 Yield

Conditions & References T= 100 - 120 °C Kikukawa, Kiyoshi; Kono, Kiyoshi; Nagira, Kazuhiko; Wada, Fumio; Matsuda, Tsutomu; Tetrahedron Letters; vol. 21; (1980); p. 2877 - 2878 View in Reaxys Time= 1h, T= 100 - 120 °C , p= 10Torr , Yield given Kikukawa, Kiyoshi; Kono, Kiyoshi; Nagira, Kazuhiko; Wada, Fumio; Matsuda, Tsutomu; Journal of Organic Chemistry; vol. 46; (1981); p. 4413 - 4416 View in Reaxys bei der Destillation Gerhardt; Annales de Chimie (Cachan, France); vol. <3> 37; (1853); p. 300; Justus Liebigs Annalen der Chemie; vol. 87; (1853); p. 73 View in Reaxys Autenrieth; Chemische Berichte; vol. 34; (1901); p. 163 View in Reaxys

(v2)

Rx-ID: 1897978 View in Reaxys 178/501 Yield

Conditions & References With triethyl phosphite in chloroform-d1, dichloromethane, T= 15 - 43 °C , other solvent (CDCl3), various temperatures (5-43 deg C), Kinetics, Mechanism, Rate constant Bach, Robert D.; Rajan, Sundar J.; Vardhan, Harsha B.; Lang, Timothy J.; Albrecht, Norman G.; Journal of the American Chemical Society; vol. 103; nb. 26; (1981); p. 7727 - 7734 View in Reaxys

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With triethyl phosphite in dichloromethane, T= 15 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.), Thermodynamic data Bach, Robert D.; Rajan, Sundar J.; Vardhan, Harsha B.; Lang, Timothy J.; Albrecht, Norman G.; Journal of the American Chemical Society; vol. 103; nb. 26; (1981); p. 7727 - 7734 View in Reaxys O O

O O

Rx-ID: 1994621 View in Reaxys 179/501 Yield

Conditions & References With heteropoly acid, T= 60 °C Matsuo, Kazuhiro; Urabe, Kazuo; Izumi, Yusuke; Chemistry Letters; (1981); p. 1315 - 1316 View in Reaxys O O

N O

Rx-ID: 2047370 View in Reaxys 180/501 Yield

Cl O Te

Rx-ID: 2051017 View in Reaxys 181/501 Yield

Conditions & References

81 %, 89 %

With acetyl chloride in chloroform, Time= 5h, Heating Sadekov, I. D.; Rivkin, B. B.; Maksimenko, A. A.; Journal of Organic Chemistry USSR (English Translation); vol. 17; nb. 9; (1981); p. 1797; Zhurnal Organicheskoi Khimii; vol. 17; nb. 9; (1981); p. 2013 - 2014 View in Reaxys

O O

O N

O O

O N

Rx-ID: 2155990 View in Reaxys 182/501 Yield

Conditions & References Time= 1h, T= 100 - 120 °C , p= 10Torr , Yield given

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Kikukawa, Kiyoshi; Kono, Kiyoshi; Nagira, Kazuhiko; Wada, Fumio; Matsuda, Tsutomu; Journal of Organic Chemistry; vol. 46; (1981); p. 4413 - 4416 View in Reaxys

O O

Rx-ID: 2192473 View in Reaxys 183/501 Yield

O O

Rx-ID: 2202864 View in Reaxys 184/501 Yield

O O

Rx-ID: 2203401 View in Reaxys 185/501 Yield

Conditions & References Time= 1h, T= 100 - 120 °C , p= 10Torr , Yield given Kikukawa, Kiyoshi; Kono, Kiyoshi; Nagira, Kazuhiko; Wada, Fumio; Matsuda, Tsutomu; Journal of Organic Chemistry; vol. 46; (1981); p. 4413 - 4416 View in Reaxys Time= 1h, T= 100 - 120 °C , p= 10Torr , other educts Kikukawa, Kiyoshi; Kono, Kiyoshi; Nagira, Kazuhiko; Wada, Fumio; Matsuda, Tsutomu; Journal of Organic Chemistry; vol. 46; (1981); p. 4413 - 4416 View in Reaxys

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O O

E H 2N O

OH O

O O

O N

O O O

O O

Rx-ID: 2366805 View in Reaxys 186/501 Yield

Conditions & References With pyridine, Time= 24h, Ambient temperature, Yield given. Yields of byproduct given Muroi; Haibara; Asai; et al.; Tetrahedron; vol. 37; nb. 6; (1981); p. 1123 - 1130 View in Reaxys O

O Br

O O

O Br

Rx-ID: 2540109 View in Reaxys 187/501 Yield

O I

O O

Rx-ID: 2540120 View in Reaxys 188/501 Yield

O O

Rx-ID: 3740854 View in Reaxys 189/501 Yield

Conditions & References With air, T= 100 °C , p= 7600Torr , Product distribution, Mechanism

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Bogomol'nyi, G. M.; Freidin, B. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 8; (1981); p. 1925 1926,1684 - 1685 View in Reaxys O C

Ni(COMe)(OCOMe)(PEt3)2 (2b)

Rx-ID: 5589292 View in Reaxys 190/501 Yield

Conditions & References in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given Komiya, Sanshiro; Yamamoto, Akio; Yamamoto, Takakazu; Chemistry Letters; (1981); p. 193 - 196 View in Reaxys O

NiMe(OCOMe)(PEt3)2 (1b)

Rx-ID: 5589293 View in Reaxys 191/501 Yield

Conditions & References in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given Komiya, Sanshiro; Yamamoto, Akio; Yamamoto, Takakazu; Chemistry Letters; (1981); p. 193 - 196 View in Reaxys O

PdMe(OCOMe)(PEt3)2 (1e)

Rx-ID: 5589294 View in Reaxys 192/501 Yield

Conditions & References in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given Komiya, Sanshiro; Yamamoto, Akio; Yamamoto, Takakazu; Chemistry Letters; (1981); p. 193 - 196 View in Reaxys

Ni(COMe)(OCOPh)(PEt3)2 (2a)

O O

Rx-ID: 5679657 View in Reaxys 193/501 Yield

Conditions & References in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Komiya, Sanshiro; Yamamoto, Akio; Yamamoto, Takakazu; Chemistry Letters; (1981); p. 193 - 196 View in Reaxys

NiMe(OCOPh)(PEt3)2 (1a)

O O

Rx-ID: 5679658 View in Reaxys 194/501 Yield

Conditions & References in tetrahydrofuran, Time= 24h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts

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Komiya, Sanshiro; Yamamoto, Akio; Yamamoto, Takakazu; Chemistry Letters; (1981); p. 193 - 196 View in Reaxys H N

O O

Rx-ID: 25059815 View in Reaxys 195/501 Yield

Conditions & References 4.7 : EXAMPLE 4 (7) Starting from a mixture of an oil (1.66 g) of 2-(N,N-diethylamino)ethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6formyl-1,4-dihydropyridine-3-carboxylate, hydroxylamine hydrochloride (0.302 g) and sodium acetate (0.593 g) in acetic acid (12 ml) and acetic anhydride (1.8 ml) was obtained crystals (700 mg) according to a similar manner to that of Example 4-(2). These crystals were recrystallized from ethanol to give pure crystals (420 mg) of 2-(N,N-diethylamino)ethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-cyano-1,4-dihydropyridine-3-carboxylate, m.p. 150° to 152° C. Patent; Fujisawa Pharmaceutical Co., Ltd.; US4284634; (1981); (A1) English View in Reaxys 4.7 : N.M.R. (7) Starting from a mixture of an oil (1.66 g) of 2-(N,N-diethylamino)ethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6formyl-1,4-dihydropyridine-3-carboxylate, hydroxylamine hydrochloride (0.302 g) and sodium acetate (0.593 g) in acetic acid (12 ml) and acetic anhydride (1.8 ml) was obtained crystals (700 mg) according to a similar manner to that of Example 4-2). These crystals were recrystallized from ethanol to give pure crystals (420 mg) of 2-(N,N-diethylamino)ethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-cyano-1,4-dihydropyridine-3-carboxylate, m.p. 150° to 152° C. Patent; Fujisawa Pharmaceutical Co., Ltd.; US4145432; (1979); (A1) English View in Reaxys H N

N O

O O O

OO N O

Rx-ID: 25059816 View in Reaxys 196/501 Yield

Conditions & References 4.10 : EXAMPLE 4 (10) Starting from a mixture of a reddish oil (2.0 g) of 2-benzyloxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6formyl-1,4-dihydropyridine-3-carboxylate, hydroxylamine hydrochloride (336.9 mg), sodium acetate (662.9 mg) in acetic acid (15 ml) and acetic anhydride (1.5 ml) was obtained crystals (767 mg) according to a similar manner to that of Example 4-(2). These crystals were recrystallized from a mixture of benzene and diethyl ether to give faint yellow crystals (450 mg) of 2-benzyloxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-cyano-1,4-dihydropyridine-3-carboxylate, m.p. 139° to 140° C. (further recrystallized from a mixture of diethyl ether and n-hexane). Patent; Fujisawa Pharmaceutical Co., Ltd.; US4284634; (1981); (A1) English View in Reaxys 4.10 : N.M.R. (10) Starting from a mixture of a reddish oil (2.0 g) of 2-benzyloxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6formyl-1,4-dihydropyridine-3-carboxylate, hydroxylamine hydrochloride (336.9 mg), sodium acetate (662.9 mg) in

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acetic acid (15 ml) and acetic anhydride (1.5 ml) was obtained crystals (767 mg) according to a similar manner to that of Example 4-2). These crystals were recrystallized from a mixture of benzene and diethyl ether to give faint yellow crystals (450 mg) of 2-benzyloxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-cyano-1,4-dihydropyridine-3-carboxylate, m.p. 139° to 140° C. (further recrystallized from a mixture of diethyl ether and n-hexane). Patent; Fujisawa Pharmaceutical Co., Ltd.; US4145432; (1979); (A1) English View in Reaxys O OO

N O

O HN

Rx-ID: 25059817 View in Reaxys 197/501 Yield

Conditions & References 4.13 : EXAMPLE 4 (13) Starting from a mixture of diethyl 2-methyl-4-(2-nitrophenyl)-6-formylmethyl-1,4-dihydropyridine-3,5-dicarboxylate, hydroxylamine hydrochloride and sodium acetate in acetic acid and acetic anhydride, was obtained an oil of diethyl 2-methyl-4-(2-nitrophenyl)-6-cyanomethyl-1,4-dihydropyridine-3,5-dicarboxylate, by applying an essentially similar manner to that of Example 4-(2). Patent; Fujisawa Pharmaceutical Co., Ltd.; US4284634; (1981); (A1) English View in Reaxys 4.13 : N.M.R. (13) Starting from a mixture of diethyl 2-methyl-4-(2-nitrophenyl)-6-formylmethyl-14-dihydropyridine-3,5-dicarboxylate, hydroxylamine hydrochloride and sodium acetate in acetic acid and acetic anhydride, was obtained an oil of diethyl 2methyl-4-(2-nitrophenyl)-6-cyanomethyl-1,4-dihydropyridine-3,5-dicarboxylate, by applying an essentially similar manner to that of Example 4-2). Patent; Fujisawa Pharmaceutical Co., Ltd.; US4145432; (1979); (A1) English View in Reaxys

O racemate

Rx-ID: 1760843 View in Reaxys 198/501 Yield

Conditions & References With ozone, gas-phase ozonolysis, Kinetics, Mechanism Kuehne, Heinz; Forster, Martin; Hulliger, Juerg; Ruprecht, Heidi; Bauder, Alfred; Guenthard, Hans-Heinrich; Helvetica Chimica Acta; vol. 63; nb. 7; (1980); p. 1971 - 1999 View in Reaxys

O– N

N+

H N

N+

Rx-ID: 2005140 View in Reaxys 199/501 Yield

Conditions & References acetate buffers, Broensted acids, Kinetics, Mechanism Ibrahim, Ibrahim T.; Williams, Andrew; Journal of the Chemical Society, Chemical Communications; nb. 1; (1980); p. 25 - 27 View in Reaxys

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O O

Br Br

Sn BrBr

P O

Rx-ID: 2168589 View in Reaxys 200/501 Yield

Conditions & References

90 %

With tin tetrabromide in dichloromethane, Time= 72h, Ambient temperature, Product distribution Muratova, A. A.; Sobanova, O. B.; Yarkova, E. G.; Khramov, A. S.; Pudovik, A. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 50; nb. 2; (1980); p. 275 - 280,217 - 221 View in Reaxys

O O

Cl P

Sn ClCl

Cl P

Sn ClCl

Rx-ID: 2168590 View in Reaxys 201/501 Yield

Conditions & References

88 %

With tin(IV) chloride in dichloromethane, Time= 72h, Ambient temperature, Product distribution Muratova, A. A.; Sobanova, O. B.; Yarkova, E. G.; Khramov, A. S.; Pudovik, A. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 50; nb. 2; (1980); p. 275 - 280,217 - 221 View in Reaxys O

O O

O P

Rx-ID: 2885178 View in Reaxys 202/501 Yield

Conditions & References T= 40 - 45 °C , p= 10Torr , new directions in reaction, Product distribution, Mechanism Al'fonsov, V. A.; Girfanova, Yu. N.; Zamaletdinova, G. U.; Batyeva, E. S.; Pudovik, A. N.; Doklady Chemistry; vol. 251; (1980); p. 99 - 101; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 251; nb. 1; (1980); p. 105 - 108 View in Reaxys

O–

–O

Rx-ID: 3555487 View in Reaxys 203/501 Yield

Conditions & References With acetate buffer, potassium chloride, T= 25 °C , β-deuterium isotope effect, Rate constant, Mechanism Kovach, Ildiko M.; Elrod, James P.; Schowen, Richard L.; Journal of the American Chemical Society; vol. 102; nb. 25; (1980); p. 7530 - 7534 View in Reaxys

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O–

–

O O

N O

Rx-ID: 3869119 View in Reaxys 204/501 Yield

1 O

Cl –

(v4)

N HH

Rx-ID: 25328866 View in Reaxys 205/501 Yield

Conditions & References c : c. In a similar way as described under b, ethyl magnesium bromide was prepared from 4.4 g (40 mmol) of ethyl bromide and 1.0 g (40 mmol) of magnesium in 30 ml of diethyl ether under nitrogen. To this 2.7 g (30 mmol) of 1,4-heptadiyn were added and the mixture was heated at 40° C., gas being evolved. After the reaction had been completed the yellow-coloured mixture was filtered and in a nitrogen atmosphere added to 6.6 g (30 mmol) of 2-(6-chloro-trans-4-hexenyloxy)tetrahydropyran) in 20 ml of diethyl ether to which also 0.5 g of CuCl had been added. A strongly exothermic reaction occurred, a system being formed consisting of two layers. After approximately 2 hours, 40 ml of dry tetrahydrofuran, were added whereupon the mixture, while being stirred, was kept at ambient temperature for one night. Then 50 ml of a saturated NH4 Cl solution and 2 g of KCN were added and the mixture was extracted with diethyl ether. The extract was washed with a 20percent NaCl solution to neutral, dried (MgSO4) and evaporated, 8.2 g of an oil remaining. With 40 ml of glacial acetic acid and 20 ml of acetic acid anhydride the oil obtained was converted into the acetate, which after distillation was recovered in an amount of 1.5 g, as a fraction boiling at 115°-120° C./0.03 mm of mercury. With potassium cyanide, magnesium, copper(l) chloride in tetrahydrofuran, diethyl ether, acetic acid Patent; Nederlandse Organisatie Voor Toegepast-Natuurwetenschappe-Lijk Onderzoek Ten Behoeve Van Nijverheid, Handel En-Verkeer; US4188374; (1980); (A1) English View in Reaxys O

Rx-ID: 25334169 View in Reaxys 206/501 Yield

Conditions & References 13.ii : EXAMPLE 13 (ii) A mixture of 23.4 parts of the secondary amine described above, 8.0 parts of liquefied ethyleneoxide, 100 parts of acetic acid and 100 parts of water is stirred in a closed vessel at room temperature for 5 hours. The hydroxyethylated product STR47 recovered from the reaction mixture by the complete removal of solvent is then acetylated by heating with 50 ml of acetic anhydride on boiling water-bath for 30 minutes. 32.0 Parts of the acetyl derivative STR48 are then formylated according to the procedure described in example 6 and the formyl derivative STR49 is hydrolyzed according to procedure used in example 6 to yield the salicylaldehyde derivative STR50 solution in 150 parts of chlorobenzene. With acetic acid in water Patent; Ciba-Geigy Corporation; US4153618; (1979); (A1) English View in Reaxys

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1,3-Diacetyl-2,3,4,6-tetrahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid methyl ester [N,N'-diacetyldehydrobiotin methyl ester]

Rx-ID: 25283153 View in Reaxys 207/501 Yield

Conditions & References 12 : 1,3-Diacetyl-2,3,4,6-tetrahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid methyl ester [N,N'-diacetyldehydrobiotin methyl ester] EXAMPLE 12 1,3-Diacetyl-2,3,4,6-tetrahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid methyl ester [N,N'-diacetyldehydrobiotin methyl ester] 25.0 g. of dehydrobiotin in 350 ml. of dry methanol was brought to reflux. Approximately 15 drops of concentrated sulfuric acid were added and the solution was refluxed for 6 hours. The solvent was removed and the products (a mixture of 6a-methoxy-2-oxo-hexahydro-1H-thieno[3,4-d]imidazole-4pentanoic acid methyl ester and 3a-methoxy-2-oxo-hexahydro-1H-thieno[3,4-d]imidazole-4-pentanoic acid methyl ester) were dissolved in 150 ml. chloroform and washed with 100 ml. saturated NaHCO3 solution. After drying the chloroform with Na2 SO4 and its removal, 33.58 g. of the intermediate oily product were isolated. The above crude intermediate was mixed with 200 ml. of distilled anhydride. The solution was heated under an inert atmosphere for 4 hours. Stripping of acetic anhydride yielded a light amber oil. The N,N'-diacetyldehydrobiotin methyl ester was then eluted through a silica plug with methylene chloride. Stripping of the methylene chloride yielded a colorless crystalline product (30.9 g., 88percent yield). Patent; Hoffmann-La Roche Inc.; US4130712; (1978); (A1) English View in Reaxys

racemic cis 1,2,3,4,5,6-hexahydro-3-allyl-6-ethyl-11-methyl-8-acetoxy-2,6-methano-3-benzazocine

Rx-ID: 25283154 View in Reaxys 208/501 Yield

Conditions & References 1.B : 1,2,3,4,5,6-Hexahydro-3-allyl-6-ethyl-11-methyl-8-hydroxy-2,6-methano-3-benzazocine B. Interaction of racemic cis 1,2,3,4,5,6-hexahydro-3-allyl-6-ethyl-11-methyl-8-hydroxy-2,6-methano-3-benzazocine with acetic anhydride yielded racemic cis 1,2,3,4,5,6-hexahydro-3-allyl-6-ethyl-11-methyl-8-acetoxy-2,6-methano-3-benzazocine (Formula I: Z = --CH2 --CH=CH2; R1 = --C2 H5; R2 = --CH3; R3 = --CO--CH3), having the molecular formula C20 H27 NO2, as a thick yellow oil. Patent; Sterling Drug Inc.; US4105659; (1978); (A1) English View in Reaxys O

Rx-ID: 25282999 View in Reaxys 209/501 Yield

Conditions & References 9 : 3,6-Dimethyl-5-hepten-2-one 3,6-Dimethyl-5-hepten-2-one according to Helv. Chim. Acta 30, 2213 (1947). According to a procedure analogous to that described in paragraph c) of Example 1, the bromide obtained above (312 g.) was added at a temperature comprised between -5° and -10° to acetylacetate (obtained from 38.5 g. of sodium and 250 g. of ethyl α-Methyl acetylacetate) in 940 ml. of ethanol. The reaction mixture was allowed to react during 2 days at 20° and, after the usual treatments of extraction and drying (cf. Example 1, paragraph c) two fractions were obtained: Fraction I: B.p. 41-65°/0.001 Torr, 168 g. Fraction II: B.p. 65-70°/0.001 Torr, 219 g. (61 percent) of the ketoester intermediate. Residue: 17 g. With sodium in ethanol

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Patent; Firmenich SA; US3931326; (1976); (A1) English View in Reaxys O

racemate

Rx-ID: 994869 View in Reaxys 210/501 Yield

Conditions & References With ozone in pentane, Further byproducts given Griesbaum,K.; Brueggemann,J.; Chemische Berichte; vol. 105; (1972); p. 3638 - 3649 View in Reaxys O

N H

Rx-ID: 72843 View in Reaxys 211/501 Yield

Conditions & References T= 20 °C , mit der Tautomeren-Gemisch, Equilibrium constant Fleming; Philippides; Journal of the Chemical Society [Section] C: Organic; (1970); p. 2426 View in Reaxys

–O

H N

Ag2S

Rx-ID: 26113035 View in Reaxys 212/501 Yield

Conditions & References

68 %

in acetone, byproducts: (C6H11NH)2CO; at room temp.; Hata, T.; Tajima, K.; Mukaiyama, T.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 2746 - 2747 View in Reaxys vol. Ag: MVol.B5; 2.2.7.5, page 127 - 128 ; (from Gmelin) View in Reaxys

–O

Ag+

Ag2S

Rx-ID: 26092314 View in Reaxys 213/501 Yield

Conditions & References in neat (no solvent), closed tube, 140°C; Jezdic, V.; Razumenic, N.; Bull. Boris Kidrich Inst. Nucl. Sci.; vol. 17; (1966); p. 311 - 315; C. A.; vol. 67; (1967); p. 63679 View in Reaxys vol. Ag: MVol.B5; 2.2.7.4, page 127 - 127 ; (from Gmelin) View in Reaxys O

–O

Cl –

Pb2+

O– Pb2+

(v0)

Yield

Rx-ID: 26114790 View in Reaxys 214/501

Conditions & References in acetic acid, 0.1M Pb(CH3CO2)2 soln. in CH3CO2H, addn. of acetyl chlorde (molar ratio=1:1) at 20°C;; not isolated, detected by conductometric measurements;

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Hardt, H. D.; Bollig, R.; Angewandte Chemie; vol. 77; (1965); p. 860 ; (from Gmelin) View in Reaxys in acetic acid, 0.1M Pb(CH3CO2)2 soln. in CH3CO2H, addn. of acetyl chlorde (molar ratio=1:1) at 20°C;; not isolated, detected by conductometric measurements; vol. Pb: MVol.C2; 196, page 760 - 762 ; (from Gmelin) View in Reaxys –

Pb2+

Cl 2Pb

(v0)

Rx-ID: 26114791 View in Reaxys 215/501 Yield

Conditions & References in acetic acid, 0.1M Pb(CH3CO2)2 soln. in CH3CO2H, addn. of acetyl chloride (molar ratio=1:2) at 20°C;; not isolated, detected by conductometric measurements; Hardt, H. D.; Bollig, R.; Angewandte Chemie; vol. 77; (1965); p. 860 ; (from Gmelin) View in Reaxys in acetic acid, 0.1M Pb(CH3CO2)2 soln. in CH3CO2H, addn. of acetyl chloride (molar ratio=1:2) at 20°C;; not isolated, detected by conductometric measurements; vol. Pb: MVol.C2; 196, page 760 - 762 ; (from Gmelin) View in Reaxys

–O

Pb2+

Br2Pb

(v0)

Rx-ID: 26150035 View in Reaxys 216/501 Yield

Conditions & References in acetic acid, 0.1M Pb(CH3CO2)2 soln. in CH3CO2H, addn. of acetyl bromide (molar ratio=1:2) at 60°C;; not isolated, detected by conductometric measurements; Hardt, H. D.; Bollig, R.; Angewandte Chemie; vol. 77; (1965); p. 860 ; (from Gmelin) View in Reaxys in acetic acid, 0.1M Pb(CH3CO2)2 soln. in CH3CO2H, addn. of acetyl bromide (molar ratio=1:2) at 60°C;; not isolated, detected by conductometric measurements; vol. Pb: MVol.C2; 196, page 760 - 762 ; (from Gmelin) View in Reaxys Br–

–O

Pb2+

Pb2+ (v0)

(v0)

O–

Rx-ID: 26150036 View in Reaxys 217/501 Yield

Conditions & References in acetic acid, 0.1M Pb(CH3CO2)2 soln. in CH3CO2H, addn. of acetyl bromide (molar ratio=1:1) at 60°C;; not isolated, detected by conductometric measurements; Hardt, H. D.; Bollig, R.; Angewandte Chemie; vol. 77; (1965); p. 860 ; (from Gmelin) View in Reaxys in acetic acid, 0.1M Pb(CH3CO2)2 soln. in CH3CO2H, addn. of acetyl bromide (molar ratio=1:1) at 60°C;; not isolated, detected by conductometric measurements; vol. Pb: MVol.C2; 196, page 760 - 762 ; (from Gmelin) View in Reaxys

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–O

OH H 2N 2

Ag+ O

Rx-ID: 534650 View in Reaxys 218/501 Yield

Conditions & References T= 200 - 600 °C , Pyrolysis Jakerson; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1963); p. 1003; engl. Ausg. S. 914 View in Reaxys

–O

OH H 2N 2

Cu 2+

Rx-ID: 534657 View in Reaxys 219/501 Yield

Conditions & References T= 200 - 600 °C , Pyrolysis Jakerson; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1963); p. 1003; engl. Ausg. S. 914 View in Reaxys

–O

Ag+

Ag2O

Rx-ID: 26113011 View in Reaxys 220/501 Yield

Conditions & References

93 %, 96 %

in neat (no solvent), byproducts: Ag, CO2; 300-400°C, quartz-tube, Ar-atmosphere (1atm.), exclusion of H2O; Kirschenbaum, a. D.; Streng, A. G.; Hauptschein, M.; Journal of the American Chemical Society; vol. 75; (1953); p. 3141 - 3145 View in Reaxys vol. Ag: MVol.B5; 2.2.7.2, page 125 - 126 ; (from Gmelin) View in Reaxys in neat (no solvent), calculation of change of free enthalpy during thermic decompn.; Yakerson, V. I.; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1963); p. 914 - 921; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1963); p. 1003 - 1011 View in Reaxys vol. Ag: MVol.B5; 2.2.7.2, page 125 - 126 ; (from Gmelin) View in Reaxys

–O

O S

-2

Na +

(v1)

2 Na +

(v1)

S O

Rx-ID: 26108235 View in Reaxys 221/501 Yield

Conditions & References below -5°C Gilbert, E. E.; Chemical Reviews (Washington, DC, United States); vol. 62; (1962); p. 549 - 589 View in Reaxys vol. S: SVol.3; 3.1.7.7.3, page 315 - 316 ; (from Gmelin) View in Reaxys

N O–

O Na +

Cl (v2)

–I

+ Cl Na

(v1)

Rx-ID: 26114815 View in Reaxys 222/501 Yield

Conditions & References With iodine in not given, 40 - 50°C; evapn. Vitaller-Alba, A.; Univ. Ovideo. Rev.Fac. Cienc.; vol. 2; (1961); p. 25 - 82; C.A.; vol. 58; (1963); p. 2125 ; (from Gmelin)

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View in Reaxys With I2 in not given, 40 - 50°C; evapn. vol. Na: SVol.3; 1.8.2.1, page 1006 - 1011 ; (from Gmelin) View in Reaxys O

Na +

O–

Rx-ID: 26114816 View in Reaxys 223/501 Yield

Conditions & References With iodine, byproducts: ICl, I2O5; using excess of CH3COCl Vitaller-Alba, A.; Univ. Ovideo. Rev.Fac. Cienc.; vol. 2; (1961); p. 25 - 82; C.A.; vol. 58; (1963); p. 2125 ; (from Gmelin) View in Reaxys With I2, byproducts: ICl, I2O5; using excess of CH3COCl vol. Na: SVol.3; 1.8.2.1, page 1006 - 1011 ; (from Gmelin) View in Reaxys

P O

O O P

P O

Rx-ID: 248033 View in Reaxys 224/501 Yield

Conditions & References Erhitzen im Vakuum Petrow; Neimyschewa; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 1822,1824;engl.Ausg.S.1793,1795 View in Reaxys

–O

Hg 2+

Cl 2Hg

Rx-ID: 26114794 View in Reaxys 225/501 Yield

Conditions & References in not given, 8h heating with reflux Paul, R. C.; Singh, D.; Sandru, S. S.; Journal of the Chemical Society; (1959); p. 319 - 322 ; (from Gmelin) View in Reaxys in not given, 8h heating with reflux vol. Hg: MVol.B3; 6.21.6, page 1283 - 1288 ; (from Gmelin) View in Reaxys O

HN O

N O

H 2N

NH 2

Rx-ID: 335581 View in Reaxys 226/501 Yield

Conditions & References Ridel'; Gertschuk; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 1306,1308;engl.Ausg.S.1365 View in Reaxys

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O O

O racemate

Rx-ID: 416940 View in Reaxys 227/501 Yield

Conditions & References T= 520 °C , Pyrolysis Wiberg; Barnes; Journal of Organic Chemistry; vol. 23; (1958); p. 229 View in Reaxys

HO O

racemate

Rx-ID: 417239 View in Reaxys 228/501 Yield

Conditions & References T= 500 °C Wiberg; Barnes; Journal of Organic Chemistry; vol. 23; (1958); p. 299 View in Reaxys

tetraacetyl diborate

Rx-ID: 7087653 View in Reaxys 229/501 Yield

Conditions & References Gerrard et al.; Journal of the Chemical Society; (1958); p. 3648,3651 View in Reaxys

O O

tetraacetyl diborate

Rx-ID: 7087654 View in Reaxys 230/501 Yield

Conditions & References Gerrard et al.; Journal of the Chemical Society; (1958); p. 3648,3651 View in Reaxys

Cl Cl

O O

Rx-ID: 3640 View in Reaxys 231/501 Yield

Conditions & References Horner; Juergens; Justus Liebigs Annalen der Chemie; vol. 602; (1957); p. 135,141, 145 View in Reaxys

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S O

Rx-ID: 211474 View in Reaxys 232/501 Yield

Conditions & References Horner; Juergens; Justus Liebigs Annalen der Chemie; vol. 602; (1957); p. 135,141, 145 View in Reaxys –

Cl O

Na +

Rx-ID: 217389 View in Reaxys 233/501 Yield

Conditions & References Heslinga et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 76; (1957); p. 969,972 View in Reaxys

O O

OH O

H 2N 2

Rx-ID: 252197 View in Reaxys 234/501 Yield

Conditions & References Pyrolysis Gutbier; Plust; Chemische Berichte; vol. 88; (1955); p. 1777 View in Reaxys Nerdel; Kleinwaechter; Chemische Berichte; vol. 90; (1957); p. 598 View in Reaxys

–O

Ag+

Rx-ID: 534649 View in Reaxys 235/501 Yield

Conditions & References With bis-chlorodiphenylmethane, T= 100 - 110 °C Jewlampijew; Zhurnal Obshchei Khimii; vol. 7; (1937); p. 2938; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 1747 View in Reaxys With carbon disulfide, T= 165 °C Broughton; ; (1865); p. 306 View in Reaxys With disulfur dichloride, diethyl ether, bei der Zersetzung der entstehenden Verbindung Denham; Journal of the Chemical Society; vol. 95; (1909); p. 1238 View in Reaxys With carbon disulfide, T= 150 °C Bryce-Smith; Proceedings of the Chemical Society, London; (1957); p. 20 View in Reaxys

O Cl

Cl O

Rx-ID: 713270 View in Reaxys 236/501 Yield

Conditions & References T= 25 - 100 °C , Rate constant

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Bell; Lukianenko; Journal of the Chemical Society; (1957); p. 1686 View in Reaxys O

Cl Cl

Sn ClCl

Rx-ID: 7058110 View in Reaxys 237/501 Yield

Conditions & References T= 25 - 100 °C , Rate constant Bell; Lukianenko; Journal of the Chemical Society; (1957); p. 1686 View in Reaxys

–O

Na +

sodium poly phosphate Rx-ID: 8236325 View in Reaxys 238/501

Yield

Conditions & References T= 280 - 600 °C , Pyrolysis Salih; Hisar; Bulletin de la Societe Chimique de France; (1956); p. 1259,1261 View in Reaxys –O

– 4 Na + O

Na +

Na 2O6P2

O–O– P

O P

O–

Rx-ID: 26151055 View in Reaxys 239/501 Yield

Conditions & References in neat (no solvent), at 280-370°C; Remziye, S. H.; Bulletin de la Societe Chimique de France; (1956); p. 1259 - 1262 View in Reaxys vol. Na: SVol.4; 22, page 1415 - 1417 ; (from Gmelin) View in Reaxys in neat (no solvent), byproducts: C; at 400°C; Remziye, S. H.; Bulletin de la Societe Chimique de France; (1956); p. 1259 - 1262 View in Reaxys vol. Na: SVol.4; 22, page 1415 - 1417 ; (from Gmelin) View in Reaxys O–

O P

3 Na + –O

P O

–O

O Na +

– 4 Na + O

O–O– P

O P

O–

Rx-ID: 26465065 View in Reaxys 240/501 Yield

Conditions & References in neat (no solvent), start of react. >280°C; Hisar, R. S.; Bulletin de la Societe Chimique de France; (1956); p. 1259 - 1262 ; (from Gmelin) View in Reaxys in neat (no solvent), start of react. >280°C; vol. Na: SVol.4; 134, page 1655 - 1657 ; (from Gmelin) View in Reaxys

Rx-ID: 239284 View in Reaxys 241/501

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Yield

Conditions & References T= 250 - 300 °C Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys With sulfuric acid Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys With mercuric sulphate Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys Zersetzung an sauren Katalysatoren Kasarnowski; Pissarew; ; vol. 1; (1936); p. 195; Chem. Zentralbl.; vol. 108; nb. I; (1937); p. 1012 View in Reaxys Patent; Dreyfus; GB447690; (1934) View in Reaxys Patent; Dreyfus; US2106798; (1935) View in Reaxys Patent; du Pont de Nemours and Co.; US2264789; (1939) View in Reaxys Zersetzung an sauren Katalysatoren Sixt; ; vol. 6; (1955); p. 806 View in Reaxys

–O

4 H

Cl 2Ni

Ni 2+

Rx-ID: 26069145 View in Reaxys 242/501 Yield

Conditions & References

<99

in benzene Watt, G. W.; Gentile, P. S.; Helvenston, E. P.; Journal of the American Chemical Society; vol. 77; (1955); p. 2752 2753; C. A.; (1955); p. 11475 ; (from Gmelin) View in Reaxys

<99

in benzene vol. Ni: MVol.B3; 44, page 865 - 867 ; (from Gmelin) View in Reaxys

O P

Rx-ID: 21520 View in Reaxys 243/501 Yield

Conditions & References T= -10 °C Cade; Gerrard; Journal of the Chemical Society; (1954); p. 2030,2033 View in Reaxys

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Rx-ID: 639057 View in Reaxys 244/501 Yield

Conditions & References Eglinton et al.; Journal of the Chemical Society; (1954); p. 1860,1864 View in Reaxys

Rx-ID: 220425 View in Reaxys 245/501 Yield

Conditions & References With 1-methyl-pyrrolidin-2-one, carbon monoxide, hydrogen, T= 190 °C , p= 514855Torr , in Gegenwart von Kobalt(II)-jodid oder Kobalt(II)-bromid Patent; BASF; US2729651; (1953) View in Reaxys Patent; BASF; US2789137; (1953) View in Reaxys O O

NH 2 O

H N

Rx-ID: 618035 View in Reaxys 246/501 Yield

Conditions & References Mechanism Fry; Journal of the American Chemical Society; vol. 75; (1953); p. 2686 View in Reaxys Naegeli; Tyabji; Helvetica Chimica Acta; vol. 17; (1934); p. 950 View in Reaxys Newman; Lee; Garrett; Journal of the American Chemical Society; vol. 69; (1947); p. 113,115 View in Reaxys

–O

O Cu 2+

air Rx-ID: 5818070 View in Reaxys 247/501

Yield

Conditions & References T= 50 °C , bei geringem Ueberdruck Patent; Eastman Kodak Co.; US2367501; (1940) View in Reaxys Sixt; ; vol. 6; (1953); p. 810 View in Reaxys Patent; Stickstoffduenger,A.-G.; DE745644; (1941); ; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 71,73 View in Reaxys Patent; Stickstoffduenger,A.-G.; DE705641; (1934) View in Reaxys Patent; Stickstoffduenger,A.-G.; DE708822; (1934) View in Reaxys Patent; Stickstoffduenger,A.-G.; DE694699; (1933) View in Reaxys Patent; Stickstoffduenger,A.-G.; DE699709; (1934) View in Reaxys Benson; ; vol. 47; (1940); p. 150

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View in Reaxys Patent; Shawinigan Chem.Ltd.; US2170002 View in Reaxys –

Cu 2+

air Rx-ID: 5818071 View in Reaxys 248/501

Yield

air

cobalt acetate Rx-ID: 5818073 View in Reaxys 249/501

Yield

91/149

2016-05-09 22:47:20

air

cobalt acetate Rx-ID: 5818074 View in Reaxys 250/501

Yield

air

manganese acetate Rx-ID: 5818076 View in Reaxys 251/501

Yield

air

manganese acetate Rx-ID: 5818077 View in Reaxys 252/501

Yield

Conditions & References T= 50 °C , bei geringem Ueberdruck

92/149

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Patent; Eastman Kodak Co.; US2367501; (1940) View in Reaxys Sixt; ; vol. 6; (1953); p. 810 View in Reaxys Patent; Stickstoffduenger,A.-G.; DE745644; (1941); ; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 71,73 View in Reaxys Patent; Stickstoffduenger,A.-G.; DE705641; (1934) View in Reaxys Patent; Stickstoffduenger,A.-G.; DE708822; (1934) View in Reaxys Patent; Stickstoffduenger,A.-G.; DE694699; (1933) View in Reaxys Patent; Stickstoffduenger,A.-G.; DE699709; (1934) View in Reaxys Benson; ; vol. 47; (1940); p. 150 View in Reaxys Patent; Shawinigan Chem.Ltd.; US2170002 View in Reaxys O

ZnCl2 O

4-oxo-2.2.6-trimethyl-1.3-dioxime

Rx-ID: 5847262 View in Reaxys 253/501 Yield

Conditions & References T= 100 °C Naylor; Journal of the Chemical Society; (1945); p. 244 View in Reaxys Carroll; Bader; Journal of the American Chemical Society; vol. 75; (1953); p. 5400 View in Reaxys O

OH O

H 2N 2

carbon monoxide Rx-ID: 7071035 View in Reaxys 254/501

Yield

Conditions & References Zersetzung Edwards; Henley; Journal of the American Chemical Society; vol. 75; (1953); p. 3587 View in Reaxys

–

Ag+ O

H 2N 2

silver oxide

silver Rx-ID: 8287086 View in Reaxys 255/501

Yield

Conditions & References T= 300 - 400 °C , unter Argon.Pyrolysis Kirshenbaum et al.; Journal of the American Chemical Society; vol. 75; (1953); p. 3141,3143 View in Reaxys

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O O

O2Si

O O

Rx-ID: 26728079 View in Reaxys 256/501 Yield

Conditions & References in neat (no solvent), decompn. of Si(OOCCH3)4 at 160-170°C and 1 atm; Friedel, C.; Ladenburg, A.; Liebigs Annalen der Chemie; vol. 145; (1868); p. 174 - 178 View in Reaxys Vol'nov, Ju. N.; Zhurnal Obshchei Khimii; vol. 9; (1939); p. 2269 - 2282; C. I; (1940); p. 2307 View in Reaxys Patent; Malatesta, L.; IT436808; (1948); C. A.; (1950); p. 4489 View in Reaxys Balthis, J. H.; Bailar, J. C., Inorganic syntheses, Bd. 4, New York-Toronto-London 1953, S. 45/47 ; (from Gmelin) View in Reaxys in neat (no solvent), decompn. of Si(OOCCH3)4 at 160-170°C and 1 atm; Goubeau, J.; Mundiel, R.; Z. Anorg. Chem.; vol. 272; (1953); p. 313 - 325 View in Reaxys Malatesta, L.; Gazzetta Chimica Italiana; vol. 78; (1948); p. 753 - 763 View in Reaxys Schuyten, H. A.; Weaver, J. W.; Reid, D.; Journal of the American Chemical Society; vol. 69; (1947); p. 2110 2112 View in Reaxys vol. Si: MVol.C; 121, page 337 - 342 ; (from Gmelin) View in Reaxys

–O

Ag+

silver phosphite

Rx-ID: 8287044 View in Reaxys 257/501 Yield

Conditions & References Anderson; Journal of the American Chemical Society; vol. 74; (1952); p. 2371 View in Reaxys O

H O–

N+ HH

O K+

O S

O–

–O 2 NH + 4

O–

N HH

–O

S O–

Rx-ID: 26107841 View in Reaxys 258/501 Yield

Conditions & References -70°C, ratio of (NH4)2S2O5, (NH4)2SO3 89, 11percent Behne, W.; Jander, G.; Hecht, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 269; (1952); p. 249 261 ; (from Gmelin) View in Reaxys -70°C, ratio of (NH4)2S2O5, (NH4)2SO3 89, 11percent vol. S: SVol.3; 2.1.8.10.8, page 217 - 218 ; (from Gmelin) View in Reaxys

O O

Rx-ID: 232179 View in Reaxys 259/501

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Yield

Conditions & References T= 30 °C , bei der Destillation Elkik; Gault; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 232; (1951); p. 2225; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 238; p. 2430 View in Reaxys

–O

Co 2+

Rx-ID: 639234 View in Reaxys 260/501 Yield

Conditions & References Bawn; Williamson; Transactions of the Faraday Society; vol. 47; (1951); p. 721,732 View in Reaxys O

Rx-ID: 642737 View in Reaxys 261/501 Yield

Conditions & References Arens; Modderman; Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences; vol. 53; (1950); p. 1163,1166 View in Reaxys

O HO

O O

Rx-ID: 701287 View in Reaxys 262/501 Yield

Conditions & References Karrer; Hohl; Helvetica Chimica Acta; vol. 32; (1949); p. 1933 View in Reaxys

OH HO

S OO

Rx-ID: 6680226 View in Reaxys 263/501 Yield

Conditions & References anschliessende Destillation Hagemeyer; Hull; Industrial and Engineering Chemistry; vol. 41; (1949); p. 2921 View in Reaxys

OH HO

S OO

Rx-ID: 6683140 View in Reaxys 264/501 Yield

Conditions & References Hagemeyer; Hull; Industrial and Engineering Chemistry; vol. 41; (1949); p. 2921 View in Reaxys

E O

(v4)

Rx-ID: 7054819 View in Reaxys 265/501 Yield

Conditions & References Wagner; Journal of the American Chemical Society; vol. 71; (1949); p. 3216 View in Reaxys

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N2O5

Rx-ID: 7081801 View in Reaxys 266/501 Yield

Conditions & References T= -10 °C , Gleichgewicht der Reaktion Chedin; Feneant; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 229; (1949); p. 116 View in Reaxys O

glacial acetic acid<1 mol>

Rx-ID: 5690275 View in Reaxys 267/501 Yield

Conditions & References With sulfuric acid Patent; Eastman Kodak Co.; US2476859; (1948) View in Reaxys O

glacial acetic acid<2 mol>

Rx-ID: 5690276 View in Reaxys 268/501 Yield

Conditions & References T= 25 °C Patent; Eastman Kodak Co.; US2476859; (1948) View in Reaxys O

B O

Rx-ID: 7061529 View in Reaxys 269/501 Yield

Conditions & References Hauser; Swamer; Ringler; Journal of the American Chemical Society; vol. 70; (1948); p. 4023,4025 View in Reaxys

sodium

Rx-ID: 7448115 View in Reaxys 270/501 Yield

Conditions & References Clemo; King; Journal of the Chemical Society; (1948); p. 1661,1665 View in Reaxys

–O

O Na +

S Cl

Rx-ID: 730094 View in Reaxys 271/501 Yield

Conditions & References T= 230 °C Shepherd; Journal of Organic Chemistry; vol. 12; (1947); p. 275,278, 280 View in Reaxys

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–O

O O

Na +

S Cl

O –O

Na +

Rx-ID: 730095 View in Reaxys 272/501 Yield

Conditions & References T= 230 °C Shepherd; Journal of Organic Chemistry; vol. 12; (1947); p. 275,278, 280 View in Reaxys

Rx-ID: 239285 View in Reaxys 273/501 Yield

Conditions & References With zinc Patent; Bayer and Co.; DE360325; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 250 View in Reaxys With acetic acid, zinc(II) chloride, zinc Patent; Usines du Rhone; DE451533; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 128 View in Reaxys With acetic acid, zinc dibromide, zinc Patent; Usines du Rhone; DE451533; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 128 View in Reaxys With phosphoric acid Patent; Shawinigan Water and Power Co.; DE408416; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 203 View in Reaxys With sulfuric acid, nitrobenzene Patent; Verein f.chem.Ind.A.G.; DE495334; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 182 View in Reaxys With nitrobenzene, benzenesulfonic Acid Patent; Verein f.chem.Ind.A.G.; DE495334; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 182 View in Reaxys T= 250 - 300 °C Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys With sulfuric acid Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys With mercuri sulfate Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys With kieselguhr, sulfuric acid Patent; Konsortium f.elektrochem.Ind.; DE391674; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 222 View in Reaxys

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T= 220 - 320 °C , Kinetik der Thermischen Zersetzung vermindertem Druck., Kinetics Dacey; Coffin; Journal of Chemical Physics; vol. 7; (1939); p. 315 View in Reaxys Coffin; Canadian Journal of Research; vol. 5; (1931); p. 643 View in Reaxys Coffin; Dacey; Parlee; Canadian Journal of Research, Section B: Chemical Sciences; vol. 15; (1937); p. 250,252 View in Reaxys beim Erhitzen in Gegenwart verschiedener Katalysatoren Patent; Brit. Celanese Ltd.; US2425389; (1945) View in Reaxys T= 250 - 300 °C Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys

O O O

O O

Rx-ID: 379404 View in Reaxys 274/501 Yield

Conditions & References Disproportionierung Patent; Heyden Chem. Corp.; US2423569; (1945) View in Reaxys

O O

Rx-ID: 639578 View in Reaxys 275/501 Yield

Conditions & References T= 90 °C Patent; Heyden Chem.Corp.; US2423569; (1945) View in Reaxys T= 90 °C Patent; Heyden Chem.Corp.; US2423569; (1945) View in Reaxys

O O

Rx-ID: 640321 View in Reaxys 276/501 Yield

Conditions & References Patent; Heyden Chem. Corp.; US2423569; (1945) View in Reaxys

98/149

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O O

Rx-ID: 804661 View in Reaxys 277/501 Yield

Conditions & References With oxygen, T= 30 - 45 °C , mit Hilfe geeigneter Katalysatoren wie z.B.V2O5 Patent; Distillers Co.; US2405471; (1945) View in Reaxys Patent; Distillers Co.; US2405470; (1941) View in Reaxys Patent; Distillers Co.; US2403769; (1942) View in Reaxys With air, T= 30 - 45 °C , mit Hilfe geeigneter Katalysatoren wie z.B.V2O5 Patent; Distillers Co.; US2405471; (1945) View in Reaxys Patent; Distillers Co.; US2405470; (1941) View in Reaxys Patent; Distillers Co.; US2403769; (1942) View in Reaxys O O

Rx-ID: 804844 View in Reaxys 278/501 Yield

N O

CuO

CuNO3 Rx-ID: 7072929 View in Reaxys 279/501

Yield

Conditions & References Boh; Annales de Chimie (Cachan, France); vol. <11>20; (1945); p. 437 View in Reaxys Chretien; Boh; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 220; (1945); p. 823 View in Reaxys

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MgNO3

MgO

Rx-ID: 7081207 View in Reaxys 280/501 Yield

PbNO3

PbO

Rx-ID: 7084267 View in Reaxys 281/501 Yield

–O

Na +

Rx-ID: 534717 View in Reaxys 282/501 Yield

Conditions & References With SCl2, chlorine, T= 15 - 20 °C Patent; AGFA; DE273101; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 70 View in Reaxys With dinitrogen tetraoxide, bei Abwesenheit von Luft Rodionow; Oblitzewa; ; (1940); p. 6572; Chem. Zentralbl.; vol. 109; nb. II; (1938); p. 4054 View in Reaxys With bromine, acetic anhydride, sulfur Orshanski; Bograchow; Chemistry and Industry (London, United Kingdom); (1944); p. 382; ; (1945); p. 3253 View in Reaxys With sulfuryl dichloride Patent; Eastman Kodak Co.; US1912747; (1930) View in Reaxys Patent; U.S.Ind.Alcohol Co.; US1860542; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 268 View in Reaxys Patent; U.S.Ind.Alcohol Co.; DE546749; (1931) View in Reaxys With sodium chlorosulfonate Pytasz; Rabek; Przemysl Chemiczny; vol. 14; (1930); p. 529; Chem. Zentralbl.; vol. 102; nb. I; (1931); p. 2112 View in Reaxys Patent; BASF; DE146690; (1902) View in Reaxys With bis-chlorodiphenylmethane, T= 120 - 140 °C Jewlampijew; Zhurnal Obshchei Khimii; vol. 7; (1937); p. 2938; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 1747 View in Reaxys With bis(trichloromethyl) carbonate

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Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys With tetrachlorosilane, acetic anhydride, T= 50 °C Montonna; Journal of the American Chemical Society; vol. 49; (1927); p. 2115 View in Reaxys With tetrachlorosilane, benzene, T= 50 °C Montonna; Journal of the American Chemical Society; vol. 49; (1927); p. 2115 View in Reaxys With acetyl chloride Terlinck; ; vol. 81; (1927); p. 106,166 View in Reaxys Haunschild; ; vol. 78; p. 662; Chem. Zentralbl.; vol. 97; nb. II; (1926); p. 826 View in Reaxys With α,α,α-trichlorotoluene, T= 230 - 240 °C , im Rohr Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With acetic acid, α,α,α-trichlorotoluene, unter Rueckfluss Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With acetic anhydride, α,α,α-trichlorotoluene, unter Rueckfluss Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With 4-bis-chloro-methylbenzene, T= 160 - 170 °C Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With chlorine, sulfur Fritzmann; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 1; p. 29; Chem. Zentralbl.; vol. 99; nb. II; (1928); p. 2548 View in Reaxys Patent; Th.Goldschmidt; DE222236 View in Reaxys Patent; Th.Goldschmidt; DE241898 View in Reaxys With chlorosulfonic acid Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With chlorosulfonic acid, sulfur trioxide Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With chlorosulfonic acid, sulfuryl dichloride Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With chlorosulfonic acid, sulphur pentoxydichloride

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Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With sulfuryl dichloride Gassner G.m.b.H.,Haeusler,Mc Lang; ; vol. 76; (1925); p. 787 View in Reaxys G.Cohn in F.Ullmann; View in Reaxys Terlinck; ; vol. 81; (1927); p. 106,166 View in Reaxys Haunschild; ; vol. 78; p. 662; Chem. Zentralbl.; vol. 97; nb. II; (1926); p. 826 View in Reaxys With sodium chlorosulfonate Patent; Bad. Anilin- u. Sodaf.; DE146690 View in Reaxys With phosgene, T= 140 °C Patent; Hofmann u. Schoetensack; DE29669; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 1; p. 574 View in Reaxys Hentschel; Chemische Berichte; vol. 17; (1884); p. 1285 View in Reaxys With p-toluenesulfonyl chloride Patent; Chem. Fabr. von Heyden; DE123052 View in Reaxys With sulfuryl dichloride, T= 68 - 69.5 °C Klar in F. Ullmanns; View in Reaxys With nitrogen oxides, oxygen Patent; R.Mueller,Deutsche Celluloid-Fabr.; DE287649; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 81 View in Reaxys With silicon oxychloride Zanetti; Journal of the American Chemical Society; vol. 34; (1912); p. 1599 View in Reaxys With disulfur dichloride, chlorine, T= 15 - 20 °C Patent; AGFA; DE273101; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 70 View in Reaxys With chlorine, sodium thiosulfate, T= 40 - 50 °C Patent; General Chemical Comp.; DE283163; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 75 View in Reaxys With sulfuryl dichloride Patent; AGFA; DE244602; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 10; p. 68 View in Reaxys With tetrachloromethane, sulfur trioxide Patent; Beatty; DE290702; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 79 View in Reaxys With α,α,α-trichlorotoluene, toluene, unter Rueckfluss

102/149

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Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With disulfur dichloride, chlorosulfonic acid Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With chlorine, sulfur, T= -24 - 50 °C Patent; Goldschmidt; DE222236; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 10; p. 66,67 View in Reaxys Patent; Goldschmidt; DE241898 View in Reaxys With tetrachlorosilane in acetic anhydride, slow addn. of SiCl4 to Na acetate at 50°C; storage at 90°C, several h; Montonna, R. E.; Journal of the American Chemical Society; vol. 49; (1925); p. 2114 - 2116 View in Reaxys vol. Na: SVol.4; 22, page 1415 - 1417 ; (from Gmelin) View in Reaxys With air, N2O3 in neat (no solvent), addn. of N2O3 mixed with air to dry Na acetate; vol. Na: SVol.4; 22, page 1415 - 1417 View in Reaxys Rodionov, V. M.; Oblitseva, T. A.; Tr. VI. Vses. Mendeleev. Sezda, Bd. 2, Tl. 1 (1932) 1002/3; C. II; (1938); p. 4054 View in Reaxys Rodionov, V. M.; Smarin, A. I.; Abletsova, T. A.; Chim. Farm. Promyslennost' Nr. 2 (1935) 102/6; C. A.; (1936); p. 1740 ; (from Gmelin) View in Reaxys With tetrachlorosilane in benzene, slow addn. of SiCl4 to Na acetate at 50°C; storage at 50-60°C, several h; Montonna, R. E.; Journal of the American Chemical Society; vol. 49; (1925); p. 2114 - 2116 View in Reaxys vol. Na: SVol.4; 22, page 1415 - 1417 ; (from Gmelin) View in Reaxys O

BeO Rx-ID: 5818072 View in Reaxys 283/501 Yield

Conditions & References T= 700 °C Besson; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 218; (1944); p. 720 View in Reaxys C+

–O

-1

O K+

F (v4)

B FF

B– F

K+

Rx-ID: 26405066 View in Reaxys 284/501 Yield

Conditions & References in further solvent(s), solvent: BF3 etherate Seel, F.; Z. Anorg. Chem.; vol. 250; (1943); p. 331 - 351 ; (from Gmelin) View in Reaxys in liquid sulphur dioxide Seel, F.; Z. Anorg. Chem.; vol. 250; (1943); p. 331 - 351 ; (from Gmelin) View in Reaxys

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in sulfur dioxide vol. B: SVol.1; 4.4.5, page 187 - 196 ; (from Gmelin) View in Reaxys in further solvent(s), solvent: BF3 etherate vol. B: SVol.1; 4.4.5, page 187 - 196 ; (from Gmelin) View in Reaxys C+ -1

N1O -1

F (v4)

(v3)

F (v4)

B FF

B F F

Rx-ID: 26450012 View in Reaxys 285/501 Yield

Conditions & References With sodium nitrite, sublimation in vac. Seel, F.; Z. Anorg. Chem.; vol. 250; (1943); p. 331 - 351 ; (from Gmelin) View in Reaxys With NaNO2, sublimation in vac. vol. B: SVol.1; 4.4.5, page 187 - 196 ; (from Gmelin) View in Reaxys O

O HO

S OO

4-oxo-2.2.6-trimethyl-1.3-dioxime

Rx-ID: 5847261 View in Reaxys 286/501 Yield

Conditions & References T= 55 °C Gwynn; Degering; Journal of the American Chemical Society; vol. 64; (1942); p. 2217 View in Reaxys

Rx-ID: 240352 View in Reaxys 287/501 Yield

Conditions & References Williams; Dickert; Krynitsky; Journal of the American Chemical Society; vol. 63; (1941); p. 2511 View in Reaxys Williams; Krynitsky; View in Reaxys

Rx-ID: 637405 View in Reaxys 288/501 Yield

Conditions & References With oxygen, bei kurzer Verweilzeit unter Druck, vorteilhaft in Gegenwart von Metallsalzen, und sofortige Abtrennung von gleichzeitig entstandenem Wasser nach verschiedenen Verfahren erhalten Patent; Carbide and Carbon Chem.Corp.; US2225486; (1938) View in Reaxys Patent; Shawinigan Chem.Ltd.; US2170002; (1936) View in Reaxys Patent; Chem.Marketing Co.; US2259895; (1938)

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2016-05-09 22:47:20

View in Reaxys Patent; Celanese Corp.Am.; US2298354; (1938) View in Reaxys Patent; Eastman Kodak Co.; US2367501; (1940) View in Reaxys Patent; Degussa; CH214604; (1938) View in Reaxys Patent; Stickstoffduenger,A.G.; DE745664; (1941) View in Reaxys Patent; Stickstoffduenger,A.G.; DE705641; (1934); ; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 73 View in Reaxys Patent; Stickstoffduenger,A.G.; DE708822; (1934) View in Reaxys Patent; Stickstoffduenger,A.G.; DE694699; (1933); ; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 71 View in Reaxys Patent; Stickstoffduenger,A.G.; DE699709; (1934) View in Reaxys With ozone, bei kurzer Verweilzeit unter Druck, vorteilhaft in Gegenwart von Metallsalzen, und sofortige Abtrennung von gleichzeitig entstandenen Wasser nach verschiedenen Verfahren erhalten Patent; Carbide and Carbon Chem.Corp.; US2225486; (1938) View in Reaxys Patent; Shawinigan Chem.Ltd.; US2170002; (1936) View in Reaxys Patent; Chem.Marketing Co.; US2259895; (1938) View in Reaxys Patent; Celanese Corp.Am.; US2298354; (1938) View in Reaxys Patent; Eastman Kodak Co.; US2367501; (1940) View in Reaxys Patent; Degussa; CH214604; (1938) View in Reaxys Patent; Stickstoffduenger,A.G.; DE745664; (1941) View in Reaxys Patent; Stickstoffduenger,A.G.; DE705641; (1934); ; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 73 View in Reaxys Patent; Stickstoffduenger,A.G.; DE708822; (1934) View in Reaxys Patent; Stickstoffduenger,A.G.; DE694699; (1933); ; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 71 View in Reaxys Patent; Stickstoffduenger,A.G.; DE699709; (1934) View in Reaxys O O O

O O

Rx-ID: 257120 View in Reaxys 289/501 Yield

Conditions & References T= 272 °C , unter Ausschluss von Feuchtigkeit Arnell; Dacey; Coffin; Canadian Journal of Research, Section B: Chemical Sciences; vol. 18; (1940); p. 411 View in Reaxys

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O O

–O

Na +

Rx-ID: 288472 View in Reaxys 290/501 Yield

Conditions & References Williams; Sadle; Journal of the American Chemical Society; vol. 62; (1940); p. 2801 View in Reaxys Cl

O O

Rx-ID: 344741 View in Reaxys 291/501 Yield

Conditions & References T= 230 - 280 °C , Dissoziation in der Gasphase, Kinetics Parlee; Arnell; Coffin; Canadian Journal of Research, Section B: Chemical Sciences; vol. 18; (1940); p. 223,226, 228, 229 View in Reaxys

O O

O O O O

Rx-ID: 527930 View in Reaxys 292/501 Yield

Conditions & References Diels; Thiele; Journal fuer Praktische Chemie (Leipzig); vol. <2> 156; (1940); p. 195,200 View in Reaxys O

O HO

S OO

Rx-ID: 7444910 View in Reaxys 293/501 Yield

Conditions & References Williams; Sadle; Journal of the American Chemical Society; vol. 62; (1940); p. 2801 View in Reaxys

Ba2+– O 2

Rx-ID: 538676 View in Reaxys 294/501 Yield

Conditions & References With sodium chlorosulfonate, acetic acid Patent; Hooker Elektrochem.Co.; US2260391; (1939) View in Reaxys

O5V2

O (v5)

Cl O

Rx-ID: 26114783 View in Reaxys 295/501

106/149

2016-05-09 22:47:20

Yield

Conditions & References in neat (no solvent) Chretien, A.; Oechsel, G.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 206; (1938); p. 254 - 256 View in Reaxys vol. V: MVol.B1; 88, page 237 - 239 ; (from Gmelin) View in Reaxys

–O

Na +

O–

Rx-ID: 26156424 View in Reaxys 296/501 Yield

Conditions & References

85 %

With dinitrogen tetraoxide in neat (no solvent), byproducts: N2O3; addn. of N2O4 to dry Na acetate; vol. Na: SVol.4; 22, page 1415 - 1417 View in Reaxys Rodionov, V. M.; Oblitseva, T. A.; Tr. VI. Vses. Mendeleev. Sezda, Bd. 2, Tl. 1 (1932) 1002/3; C. II; (1938); p. 4054 View in Reaxys Rodionov, V. M.; Smarin, A. I.; Abletsova, T. A.; Chim. Farm. Promyslennost' Nr. 2 (1935) 102/6; C. A.; (1936); p. 1740 ; (from Gmelin) View in Reaxys O O

O O

Rx-ID: 229109 View in Reaxys 297/501 Yield

Conditions & References T= 210 - 280 °C , Rate constant Dacey; Coffin; Canadian Journal of Research, Section B: Chemical Sciences; vol. 15; (1937); p. 260 View in Reaxys

O Cl O

Cl Cl

Rx-ID: 250721 View in Reaxys 298/501 Yield

Conditions & References T= 210 - 290 °C , Kinetics Parlee; Dacey; Coffin; Canadian Journal of Research, Section B: Chemical Sciences; vol. 15; (1937); p. 255,258 View in Reaxys

Cl –

Ag+

Rx-ID: 282848 View in Reaxys 299/501 Yield

Conditions & References T= 100 - 110 °C , mit den Natriumsalzen anderer Carbonsaeuren erfolgen analoge Reaktionen Jewlampijew; Zhurnal Obshchei Khimii; vol. 7; (1937); p. 2938; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 1747 View in Reaxys

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–O

Na +

Rx-ID: 282849 View in Reaxys 300/501 Yield

Conditions & References T= 120 - 140 °C , mit den Natriumsalzen anderer Carbonsaeuren erfolgen analoge Reaktionen Jewlampijew; Zhurnal Obshchei Khimii; vol. 7; (1937); p. 2938; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 1747 View in Reaxys

–O

Cu 2+

Rx-ID: 534655 View in Reaxys 301/501 Yield

Conditions & References T= 150 - 250 °C , unter vermindertem Druck Patent; Dreyfus; US2073686; (1932) View in Reaxys Patent; Dreyfus; GB381963; (1931) View in Reaxys Chang; Kao; ; vol. 4; (1937); p. 160; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 1335 View in Reaxys Patent; Consort.elektrochem.Ind.; DE556247; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 266 View in Reaxys

–O

Cu 2+

Rx-ID: 534656 View in Reaxys 302/501 Yield

Conditions & References p= 11 - 300Torr , beim Erhitzen Chang; Kao; ; vol. 4; (1937); p. 162; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 1335 View in Reaxys O

chromium (III)-acetate Rx-ID: 5589287 View in Reaxys 303/501 Yield

copper (I)-acetate Rx-ID: 5589289 View in Reaxys 304/501 Yield

Conditions & References T= 150 - 250 °C , unter vermindertem Druck

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Patent; Dreyfus; US2073686; (1932) View in Reaxys Patent; Dreyfus; GB381963; (1931) View in Reaxys Chang; Kao; ; vol. 4; (1937); p. 160; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 1335 View in Reaxys Patent; Consort.elektrochem.Ind.; DE556247; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 266 View in Reaxys –O

Ag+

Rx-ID: 26113005 View in Reaxys 305/501 Yield

Conditions & References in neat (no solvent), thermic decompn.;; main-product: CH3CO2H; Iwig, F.; Hecht, O.; Ber. Dtsch. Chem. Ges.; vol. 19; (1886); p. 238 - 242 View in Reaxys Kachler, J.; Monatshefte fuer Chemie; vol. 12; (1891); p. 338 - 349 View in Reaxys vol. Ag: MVol.B5; 2.2.7.2, page 125 - 126 ; (from Gmelin) View in Reaxys in neat (no solvent), thermic decompn. under a CO2-stream of 20-25Torr;; main-product: CH3CO2H; Kanewskaja, S. J.; Schemiakin, M. M.; Ber. Dtsch. Chem. Ges.; vol. 69; (1936); p. 2152 - 2157 View in Reaxys vol. Ag: MVol.B5; 2.2.7.2, page 125 - 126 ; (from Gmelin) View in Reaxys

+Ga

Ga 2O3 O–

Rx-ID: 26633329 View in Reaxys 306/501 Yield

Conditions & References in neat (no solvent), at 159 °C; Centola, G.; 9 Congr. internac. Quim. pura apl. 3 {1934} Grupo 2, Secc. A, B, S. 231-236; C.II; (1936); p. 2322 ; (from Gmelin) View in Reaxys vol. Ga: MVol.; 41, page 94 - 95 ; (from Gmelin) View in Reaxys

Rx-ID: 101467 View in Reaxys 307/501 Yield

Conditions & References With sodium hydrogen sulphate, T= 430 - 450 °C , auf Bimsstein Patent; Dreyfus; US2116657; (1935) View in Reaxys Patent; Dreyfus; GB448452; (1934) View in Reaxys

Rx-ID: 638911 View in Reaxys 308/501

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2016-05-09 22:47:20

Yield

Conditions & References With phosphoric acid, sulfuric acid Patent; Herrmann; Deutsch; US1856251; (1928) View in Reaxys Patent; Consort.elektrochem.Ind.; DE503131; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 255,18 278 View in Reaxys Patent; Consort.elektrochem.Ind.; DE526795; (1928) View in Reaxys With phosphoric acid, phosphorus pentoxide, T= 400 - 410 °C Patent; Dreyfus; US2116657; (1935) View in Reaxys Patent; Dreyfus; GB448452; (1934) View in Reaxys With sulphur monochloride Patent; Consort.elektrochem.Ind.; DE537363; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 279 View in Reaxys With sulfuric acid Patent; Herrmann; Deutsch; US1856251; (1928) View in Reaxys Patent; Consort.elektrochem.Ind.; DE503131; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 255,18 278 View in Reaxys Patent; Consort.elektrochem.Ind.; DE526795; (1928) View in Reaxys

OH HO

P OH O

Rx-ID: 6681527 View in Reaxys 309/501 Yield

Conditions & References T= 400 - 410 °C Patent; Dreyfus; US2116657; (1935) View in Reaxys Patent; Dreyfus; GB448452; (1934) View in Reaxys

ZnCl2

cyclohexene (?) Rx-ID: 7453033 View in Reaxys 310/501

Yield

Conditions & References Underwood; Baril; Journal of the American Chemical Society; vol. 57; (1935); p. 2729 View in Reaxys

OH H

Rx-ID: 532292 View in Reaxys 311/501 Yield

Conditions & References With sodium pyrosulphate, acetic acid Patent; Dreyfuss; GB424573; (1933)

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View in Reaxys Patent; Dreyfuss; US2116656; (1934) View in Reaxys H 2N

N O

Rx-ID: 576726 View in Reaxys 312/501 Yield

Conditions & References T= 180 °C Rice et al.; Journal of the American Chemical Society; vol. 56; (1934); p. 1760,1765 View in Reaxys O

O O

N H

H 2N

O N

N H

O O

Rx-ID: 585866 View in Reaxys 313/501 Yield

Conditions & References Naegeli; Tyabji; Helvetica Chimica Acta; vol. 17; (1934); p. 950 View in Reaxys

H N

Rx-ID: 585974 View in Reaxys 314/501 Yield

Conditions & References Naegeli; Tyabji; Helvetica Chimica Acta; vol. 17; (1934); p. 950 View in Reaxys

O O

H N

H N O

H N

O N

Rx-ID: 643032 View in Reaxys 315/501 Yield

Conditions & References Naegeli; Tyabji; Helvetica Chimica Acta; vol. 17; (1934); p. 950 View in Reaxys Naegeli; Tyabji; Helvetica Chimica Acta; vol. 16; (1933); p. 349,362; Helvetica Chimica Acta; vol. 17; (1934); p. 931,950 View in Reaxys

C O

Rx-ID: 5589290 View in Reaxys 316/501 Yield

Conditions & References With hydrogenchloride, copper(l) chloride, T= -20 - -10 °C , unter hohem Druck Patent; Hale; US2117554; (1934) View in Reaxys

O O

Rx-ID: 236727 View in Reaxys 317/501

111/149

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Yield

Conditions & References bei der Destillation Hurd; Dull; Journal of the American Chemical Society; vol. 54; (1932); p. 3427,3430 View in Reaxys Patent; du Pont de Nemours and Co.; US2135709; (1933) View in Reaxys O

O O

Rx-ID: 406395 View in Reaxys 318/501 Yield

Conditions & References Hurd; Thomas; Journal of the American Chemical Society; vol. 55; (1933); p. 275,281 View in Reaxys

Rx-ID: 119970 View in Reaxys 319/501 Yield

Conditions & References With sulfuric acid, acetic acid, mercury(II) oxide, T= 45 - 50 °C Patent; I.G.Farbenind.; DE590237; (1932); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 20; p. 302 View in Reaxys O

O O

Rx-ID: 593529 View in Reaxys 320/501 Yield

Conditions & References Hurd; Dull; Journal of the American Chemical Society; vol. 54; (1932); p. 3427,3430 View in Reaxys

Rx-ID: 638739 View in Reaxys 321/501 Yield

Conditions & References With boron trifluoride, mercury(II) oxide, T= 30 °C , p= 760Torr , Ueberdruck Patent; I.G.Farbenind.; DE590237; (1932); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 20; p. 302 View in Reaxys With sulfuric acid, mercury(II) oxide, T= 30 °C , p= 760Torr , Ueberdruck Patent; I.G.Farbenind.; DE590237; (1932); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 20; p. 302 View in Reaxys

Rx-ID: 642893 View in Reaxys 322/501 Yield

Conditions & References With sulfuric acid, mercury(II) oxide, T= 30 °C , p= 760Torr , Ueberdruck Patent; I.G.Farbenind.; DE590237; (1932); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 20; p. 302 View in Reaxys

112/149

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With boron trifluoride, mercury(II) oxide, T= 30 °C , p= 760Torr , Ueberdruck Patent; I.G.Farbenind.; DE590237; (1932); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 20; p. 302 View in Reaxys

Rx-ID: 825612 View in Reaxys 323/501 Yield

Conditions & References anschliessendes Erhitzen der Reaktionsprodukte Hurd; Dull; Journal of the American Chemical Society; vol. 54; (1932); p. 3427,3430 View in Reaxys Patent; N.V.de Bataafsche Petr.Mij.; GB389042; (1932) View in Reaxys Patent; Shell Devel Co.; US2007642; (1931) View in Reaxys Williams; Krynitsky; View in Reaxys O

ethylidene acetate Rx-ID: 5589291 View in Reaxys 324/501 Yield

Conditions & References T= 320 °C , ueber mit Salzsaeure extrahierten Asbest Patent; C.F.Boehringer and Soehne; US2001211; (1932) View in Reaxys Patent; C.F.Boehringer and Soehne; FR746684; (1932) View in Reaxys Patent; C.F.Boehringer and Soehne; DE580930; (1931); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 20; p. 303 View in Reaxys

methylvinyl ketone resp. acetone Rx-ID: 5737983 View in Reaxys 325/501 Yield

(v1)

F B F

Hg (v1)

S OO

Rx-ID: 6681655 View in Reaxys 326/501 Yield

Conditions & References T= 25 - 30 °C , Neutralisieren und Destillieren des Reaktionsprodukts Patent; I.G.Farbenind.; DE590237; (1932); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 20; p. 302 View in Reaxys

O O

Rx-ID: 237671 View in Reaxys 327/501

113/149

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Yield

Conditions & References Patent; Standard Oil Devel.Co.; US2099909; (1931) View in Reaxys O

Cl O

–O

Na +

Rx-ID: 249381 View in Reaxys 328/501 Yield

Conditions & References Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys

Cl O

–

Na +

Rx-ID: 251997 View in Reaxys 329/501 Yield

Conditions & References T= 60 - 100 °C Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys

Cl Cl

O Cl

–O

Na +

H 2N 2

Rx-ID: 468096 View in Reaxys 330/501 Yield

Conditions & References T= 140 - 150 °C Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys

Cl Cl

O Cl

–O

Na +

Rx-ID: 474631 View in Reaxys 331/501 Yield

Conditions & References T= 50 - 60 °C , zuletzt bei 140-150grad Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys

Cl Cl

O Cl

–O

Na +

Rx-ID: 476528 View in Reaxys 332/501 Yield

Conditions & References T= 140 - 150 °C

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Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys O

Rx-ID: 642153 View in Reaxys 333/501 Yield

Conditions & References in hochsiedenden Loesungsmitteln, z.B.Chlornaphthalin, im Gegenstrom Patent; Degussa; DE628063; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 21; p. 158 View in Reaxys Patent; I.G.Farbenind.; US1905466; (1931) View in Reaxys Patent; I.G.Farbenind.; GB354159; (1931) View in Reaxys Patent; I.G.Farbenind.; DE546511; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 267 View in Reaxys Kanonnikow; Saizew,M.; Justus Liebigs Annalen der Chemie; vol. 185; (1877); p. 192 View in Reaxys With pyridine Wedekind; Chemische Berichte; vol. 34; (1901); p. 2070 View in Reaxys Tschitschibabin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 33; (1901); p. 406; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 543 View in Reaxys O O

Cl O

–O

Na +

Rx-ID: 7054821 View in Reaxys 334/501 Yield

Conditions & References T= 90 °C , spaeter auf 125-130grad Melnikow; Ssidorowa; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 740,742; Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2313 View in Reaxys

Rx-ID: 642617 View in Reaxys 335/501 Yield

Conditions & References T= 700 °C , ueber Porzellanstuecke Patent; N.V.de Bataafsche Petr.Mij.; DE572054; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 927 View in Reaxys Patent; N.V.de Bataafsche Petr.Mij.; US1961542; (1930) View in Reaxys O

1.1'-diacetoxy-diethyl ether Rx-ID: 5589279 View in Reaxys 336/501 Yield

Conditions & References mit Katalysatoren z.B. mit Spuren von ZnCl2 in wenig Eisessig oder SnCl2 in wenig Aceton im Vakuum

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Patent; C.F.Boehringer and Soehne; US1859786; (1930) View in Reaxys Patent; C.F.Boehringer and Soehne; FR696530; (1930) View in Reaxys Patent; C.F.Boehringer and Soehne; DE553605; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 788 View in Reaxys –O

O O

Na +

Rx-ID: 71032 View in Reaxys 337/501 Yield

Conditions & References T= 160 - 170 °C Karashima; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 180; (1929); p. 242 View in Reaxys

Rx-ID: 248914 View in Reaxys 338/501 Yield

Conditions & References in Gegenwart verschiedener Katalysatoren (z.B. ZnCl2+Eisessig, ZnCl2+Aethanol, SnCl2+Aceton, SO2) Patent; C.F. Boehringer and Soehne; FR696530 View in Reaxys Patent; C.F. Boehringer and Soehne; DE553605; (1928) View in Reaxys Patent; C.R. Boehringer and Soehne; US1859786; (1929) View in Reaxys Patent; C.R. Boehringer and Soehne; US1859785; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 788 View in Reaxys O

Rx-ID: 508316 View in Reaxys 339/501 Yield

Conditions & References Scholl; Hass; Meyer; Chemische Berichte; vol. 62; (1929); p. 113 View in Reaxys

Cl O

Rx-ID: 642180 View in Reaxys 340/501 Yield

Conditions & References T= 100 °C , Fraktionierung des Reaktionsprodukts Watson; Gregory; Journal of the Chemical Society; (1929); p. 1375 View in Reaxys T= 100 °C , so erhaelt man bei der Fraktionierung des Reaktionsprodukt unter gewoehnlichem Druck Watson; Gregory; Journal of the Chemical Society; (1929); p. 1375

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View in Reaxys O

Rx-ID: 643187 View in Reaxys 341/501 Yield

Conditions & References T= 800 °C , mit Porzellanscherben gefuelltem Quarzrohr Hurd; Martin; Journal of the American Chemical Society; vol. 51; (1929); p. 3615 View in Reaxys O

N O

Rx-ID: 663309 View in Reaxys 342/501 Yield

Conditions & References Scholl; Hass; Meyer; Chemische Berichte; vol. 62; (1929); p. 113 View in Reaxys

Rx-ID: 815761 View in Reaxys 343/501 Yield

–O

O Na +

5-acetoxymethyl-furfurol

O O

Rx-ID: 5589297 View in Reaxys 344/501 Yield

Conditions & References T= 160 - 170 °C Karashima; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 180; (1929); p. 242 View in Reaxys

oxygen

nickel carbonyl Rx-ID: 5818078 View in Reaxys 345/501

Yield

Conditions & References T= 10 °C , entsteht noch eine Verbindung von Essigsaeure mit Nickel(II)-chlorid

117/149

2016-05-09 22:47:20

Reihlen; Gruhl; v.Hessling; Justus Liebigs Annalen der Chemie; vol. 472; (1929); p. 285 View in Reaxys O

porcelain fragments

Rx-ID: 5818082 View in Reaxys 346/501 Yield

Conditions & References T= 800 °C , Leiten durch ein Quarzrohr Hurd; Martin; Journal of the American Chemical Society; vol. 51; (1929); p. 3615 View in Reaxys O

anthraquinone-carboxylic acid-(1)-anhydride O

O O

Rx-ID: 8268621 View in Reaxys 347/501 Yield

Conditions & References Scholl; Hass; Meyer; Chemische Berichte; vol. 62; (1929); p. 113 View in Reaxys O

anthraquinone-carboxylic acid-(1)-anhydride

N O

O O

Rx-ID: 8268622 View in Reaxys 348/501 Yield

Conditions & References Scholl; Hass; Meyer; Chemische Berichte; vol. 62; (1929); p. 113 View in Reaxys

O O

anthraquinone-dicarboxylic acid-(1.5)-anhydride O

O O

Rx-ID: 8268623 View in Reaxys 349/501 Yield

Conditions & References oberhalb des Schmelzpunktes Scholl; Hass; Meyer; Chemische Berichte; vol. 62; (1929); p. 113 View in Reaxys

Cl Cl

Rx-ID: 213269 View in Reaxys 350/501 Yield

Conditions & References With water, Hydrolysis Patent; Dow Chem.Co.; US1870601; (1928) View in Reaxys

118/149

2016-05-09 22:47:20

O O O

H O

Rx-ID: 453686 View in Reaxys 351/501 Yield

Conditions & References T= 190 °C Power; Moore; Journal of the Chemical Society; vol. 97; (1910); p. 1105 View in Reaxys Riviere; Pichard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 179; (1924); p. 775; Bulletin de la Societe Chimique de France; vol. <4> 37; (1925); p. 193 View in Reaxys van der Haar; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 588; Recueil des Travaux Chimiques des Pays-Bas; vol. 48; (1929); p. 611 View in Reaxys T= 190 °C Power; Moore; Journal of the Chemical Society; vol. 97; (1910); p. 1105 View in Reaxys Riviere; Pichard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 179; (1924); p. 775; Bulletin de la Societe Chimique de France; vol. <4> 37; (1925); p. 193 View in Reaxys van der Haar; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 588; Recueil des Travaux Chimiques des Pays-Bas; vol. 48; (1929); p. 611 View in Reaxys

Cl O

Rx-ID: 638917 View in Reaxys 352/501 Yield

Conditions & References T= 150 °C Patent; Hale; US1863788; (1928) View in Reaxys

OH HO

S OO

Rx-ID: 6681528 View in Reaxys 353/501 Yield

Conditions & References Patent; Consort.electrochem.Ind.; US1856251; (1928) View in Reaxys Patent; Consort.electrochem.Ind.; DE503131; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 256,18 279 View in Reaxys Patent; Consort.electrochem.Ind.; DE537363; (1928)

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View in Reaxys O

S2cl2

Rx-ID: 6681529 View in Reaxys 354/501 Yield

Cl Cl

Rx-ID: 7061158 View in Reaxys 355/501 Yield

Conditions & References T= 150 - 160 °C , unter Druck Patent; Dow Chem.Co.; US1870601; (1928) View in Reaxys

S OO

Rx-ID: 7061159 View in Reaxys 356/501 Yield

Conditions & References T= 150 - 160 °C , unter Druck Patent; Dow Chem.Co.; US1870601; (1928) View in Reaxys

Cl Cl

metal chloride Rx-ID: 7061160 View in Reaxys 357/501

Yield

Conditions & References T= 150 - 160 °C , unter Druck Patent; Dow Chem.Co.; US1870601; (1928) View in Reaxys

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2016-05-09 22:47:20

O O

H O

O O

Rx-ID: 453683 View in Reaxys 358/501 Yield

Conditions & References beim Erhitzen ueber den Schmelzpunkt Tutin; Naunton; Journal of the Chemical Society; vol. 103; (1913); p. 2050,2057 View in Reaxys Power; Tutin; Journal of the Chemical Society; vol. 93; (1908); p. 903,916 View in Reaxys van der Haar; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 788,790; Recueil des Travaux Chimiques des Pays-Bas; vol. 48; (1929); p. 611 View in Reaxys beim Erhitzen ueber den Schmelzpunkt Tutin; Naunton; Journal of the Chemical Society; vol. 103; (1913); p. 2050,2057 View in Reaxys Power; Tutin; Journal of the Chemical Society; vol. 93; (1908); p. 903,916 View in Reaxys van der Haar; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 788,790; Recueil des Travaux Chimiques des Pays-Bas; vol. 48; (1929); p. 611 View in Reaxys

2 Cr 3+ O

4 H

-2

(v1)

S O

Rx-ID: 553167 View in Reaxys 359/501 Yield

Conditions & References Recoura; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 185; (1927); p. 993 View in Reaxys

Rx-ID: 642922 View in Reaxys 360/501 Yield

Conditions & References With mercuric sulphate, in Gegenwart eines stets im Ueberschuss gehaltenen Oxydationsmittels (z.B.Chromsaeure) Patent; Degussa; DE556775; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 789 View in Reaxys

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Rx-ID: 5818069 View in Reaxys 361/501 Yield

Conditions & References Senderens; Aboulenc; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 185; (1927); p. 1088 View in Reaxys O

sulfur

Rx-ID: 5818081 View in Reaxys 362/501 Yield

Conditions & References Senderens; Aboulenc; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 185; (1927); p. 1088 View in Reaxys

Al3+ 3

O O

-2 (v1)

6 H

air

(v1)

S O

Rx-ID: 8236319 View in Reaxys 363/501 Yield

Conditions & References Recoura; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 185; (1927); p. 993 View in Reaxys

2 Cr 3+

4 H

-2

(v1)

air

(v1)

S O

Rx-ID: 8236320 View in Reaxys 364/501 Yield

Conditions & References Recoura; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 185; (1927); p. 993 View in Reaxys

2 Cr 3+

4 H

-2

(v1)

air

(v1)

S O

Rx-ID: 8236321 View in Reaxys 365/501 Yield

Conditions & References T= 25 °C Recoura; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 185; (1927); p. 993 View in Reaxys

Al3+

3 1

O O

air

(v4)

N HH

(v1)

-2

4 (v1)

S OO

Rx-ID: 8236322 View in Reaxys 366/501

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Yield

Conditions & References Recoura; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 185; (1927); p. 993 View in Reaxys

Al3+

3 1

(v4)

N HH

(v1)

-2

4 (v1)

S OO

Rx-ID: 26586555 View in Reaxys 367/501 Yield

Conditions & References in neat (no solvent), on standing in air, reversible react.; Recoura, A.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 185; (1927); p. 994 ; (from Gmelin) View in Reaxys in neat (no solvent), on standing in air, reversible react.; vol. Al: MVol.B2; 94, page 517 - 519 ; (from Gmelin) View in Reaxys

O O

B O

O B

O O

Rx-ID: 258666 View in Reaxys 368/501 Yield

Conditions & References T= 150 - 156 °C , im Vakuum Dimroth; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 114 View in Reaxys Dimroth; Faust; Chemische Berichte; vol. 54; (1921); p. 3029; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 98,108,109 View in Reaxys

O O (v3)

O B (v4) O O B (v4) (v3) O O O

O OO B O

B B

O O O

Rx-ID: 26838165 View in Reaxys 369/501 Yield

Conditions & References in neat (no solvent), at 150°C; Dimroth, O.; Schweizer, R.; Ruchti, R.; Sagstetter, K.; Hetzer, J.; et. al.; Liebigs Annalen der Chemie; vol. 446; (1926); p. 97 - 122 ; (from Gmelin) View in Reaxys in neat (no solvent), at 150°C; vol. B: B-Verb.13; 2.9, page 109 - 114 ; (from Gmelin) View in Reaxys

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Rx-ID: 181458 View in Reaxys 370/501 Yield

Conditions & References Autenrieth; Thomae; Chemische Berichte; vol. 57; (1924); p. 436 View in Reaxys T= 170 - 180 °C Autenrieth; Thomae; Chemische Berichte; vol. 57; (1924); p. 436 View in Reaxys O

acetic acid isovaleric acid anhydride Rx-ID: 5589283 View in Reaxys 371/501 Yield

Conditions & References T= 170 - 180 °C Autenrieth; Thomae; Chemische Berichte; vol. 57; (1924); p. 436 View in Reaxys

O Cu 2+

-2 (v1)

lime/chalk/

(v1)

S O

Rx-ID: 8236323 View in Reaxys 372/501 Yield

Conditions & References Recoura; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 178; (1924); p. 2220 View in Reaxys O O O O

polymer(ic) dehydrocamphoric acid anhydride O O O

Rx-ID: 8285509 View in Reaxys 373/501 Yield

Conditions & References T= 150 °C , unter vermindertem Druck, acetic acid-<dehydro-d-camphoric acid >-anhydride Bredt; Justus Liebigs Annalen der Chemie; vol. 437; (1924); p. 11,12 View in Reaxys O

O O

O HO

Rx-ID: 642091 View in Reaxys 374/501 Yield

Conditions & References T= 77.5 °C , Equilibrium constant Kremann; Roesler; Monatshefte fuer Chemie; vol. 43; (1922); p. 359 View in Reaxys

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2016-05-09 22:47:20

sodium salt of/the/ acetylsulfuric acid Rx-ID: 5589296 View in Reaxys 375/501 Yield

Conditions & References van Peski; Recueil des Travaux Chimiques des Pays-Bas; vol. 40; (1921); p. 116 View in Reaxys With sodium acetate, acetic acid van Peski; Recueil des Travaux Chimiques des Pays-Bas; vol. 40; (1921); p. 116 View in Reaxys bei der Destillation Patent; Naamlooze Vennootschap Fabr.van chemische Producten in Schiedam; DE286872; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 77 View in Reaxys With toluene, bei der Destillation Patent; Naamlooze Vennootschap Fabr.van chemische Producten in Schiedam; DE286872; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 77 View in Reaxys With acetic acid, bei der Destillation Patent; Naamlooze Vennootschap Fabr.van chemische Producten in Schiedam; DE286872; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 77 View in Reaxys bei der Destillation van Peski; ; vol. 22; (1914); p. 996 View in Reaxys With acetic acid, bei der Destillation van Peski; ; vol. 22; (1914); p. 996 View in Reaxys With toluene, bei der Destillation van Peski; ; vol. 22; (1914); p. 996 View in Reaxys O

potassium compound of acetic acid ethyl ester

O O

Rx-ID: 5818136 View in Reaxys 376/501 Yield

Conditions & References Scheibler; Voss; Chemische Berichte; vol. 53; (1920); p. 384 View in Reaxys

OH S F

O O

Rx-ID: 5818083 View in Reaxys 377/501 Yield

Conditions & References Traube; Krahmer; Chemische Berichte; vol. 52; (1919); p. 1296 View in Reaxys

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α-disalicylide

HO O

Rx-ID: 6076053 View in Reaxys 378/501 Yield

Conditions & References bei der Destillation unter vermindertem Druck Anschuetz; Chemische Berichte; vol. 52; (1919); p. 1891 View in Reaxys O O O

α-disalicylide

β-disalicylide

Rx-ID: 7441816 View in Reaxys 379/501 Yield

Conditions & References p= 12Torr , bei der Destillation Anschuetz; Chemische Berichte; vol. 52; (1919); p. 1891 View in Reaxys

(v0)

Bi3+– O 3

–O

+Bi

Rx-ID: 26459520 View in Reaxys 380/501 Yield

Conditions & References heating starting material at 125 to 130 °C over a long period in a drying cabinet; Salkowski; Biochemische Zeitschrift; vol. 79; (1917); p. 101 - 101 View in Reaxys vol. Bi: MVol.; 71, page 179 - 181 ; (from Gmelin) View in Reaxys

S O

Rx-ID: 378239 View in Reaxys 381/501 Yield

Conditions & References T= 300 °C , p= 15 - 17Torr Anschuetz; Rhodius; Chemische Berichte; vol. 47; (1914); p. 2733 View in Reaxys Mayer,F.; Chemische Berichte; vol. 42; (1909); p. 1133 View in Reaxys O

sodium salt of/the/ acetylenesulfuric acid Rx-ID: 5589295 View in Reaxys 382/501 Yield

Conditions & References With sodium acetate, acetic acid, bei der Destillation Patent; Naamlooze Vennootschap Fabr.van chemische Producten in Schiedam; DE286872; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 77 View in Reaxys

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With sodium acetate, acetic acid, bei der Destillation van Peski; ; vol. 22; (1914); p. 996 View in Reaxys O

Rx-ID: 690231 View in Reaxys 383/501 Yield

Conditions & References Diels; Okada; Chemische Berichte; vol. 44; (1911); p. 3335 View in Reaxys T= 25 °C Diels; Okada; Chemische Berichte; vol. 44; (1911); p. 3335 View in Reaxys

potassium nitrate Rx-ID: 5818079 View in Reaxys 384/501 Yield

Conditions & References T= 25 °C Diels; Okada; Chemische Berichte; vol. 44; (1911); p. 3335 View in Reaxys

nitrogen oxides

Rx-ID: 7082441 View in Reaxys 385/501 Yield

Conditions & References Diels; Okada; Chemische Berichte; vol. 44; (1911); p. 3335 View in Reaxys O O

O O

Rx-ID: 250041 View in Reaxys 386/501 Yield

Conditions & References beim Kochen Semmler; Chemische Berichte; vol. 42; (1909); p. 1161 View in Reaxys

H O

Rx-ID: 643188 View in Reaxys 387/501 Yield

Conditions & References With phosgene, 4-bis-chloro-methylbenzene Behal; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 180 View in Reaxys

benzoic acid anhydrid, acetic acid benzoic acid anhydride, benzoic acid , glacial acetic acid Rx-ID: 5726050 View in Reaxys 388/501

127/149

2016-05-09 22:47:20

Yield

Conditions & References With α,α,α-trichlorotoluene Behal; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 648 View in Reaxys With benzoyl chloride Behal; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 648 View in Reaxys

N O

H N

H N O

Rx-ID: 6082295 View in Reaxys 389/501 Yield

Conditions & References Dains; Journal of the American Chemical Society; vol. 21; (1899); p. 191 View in Reaxys Busch; Blume; Pungs; Journal fuer Praktische Chemie (Leipzig); vol. <2>79; (1909); p. 537 View in Reaxys Schall; Chemische Berichte; vol. 27; (1894); p. 2696 View in Reaxys

O O

acetic benzoic anhydride HO

Rx-ID: 6209291 View in Reaxys 390/501 Yield

Conditions & References Behal; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 648 View in Reaxys

Rx-ID: 6680950 View in Reaxys 391/501 Yield

Conditions & References Kinetics Behal; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 180 View in Reaxys –

Ag+

O S

Rx-ID: 26113027 View in Reaxys 392/501 Yield

128/149

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vol. S: MVol.B3; 116, page 1778 - 1780 ; (from Gmelin) View in Reaxys in benzene vol. S: MVol.B3; 116, page 1778 - 1780 ; (from Gmelin) View in Reaxys –O

Na +

O S

Rx-ID: 26151158 View in Reaxys 393/501 Yield

Conditions & References in diethyl ether, on heating; Denham, W. S.; Journal of the Chemical Society; vol. 95; (1909); p. 1235 - 1240 ; (from Gmelin) View in Reaxys in benzene, on heating; Denham, W. S.; Journal of the Chemical Society; vol. 95; (1909); p. 1235 - 1240 ; (from Gmelin) View in Reaxys in diethyl ether vol. S: MVol.B3; 116, page 1778 - 1780 ; (from Gmelin) View in Reaxys in benzene vol. S: MVol.B3; 116, page 1778 - 1780 ; (from Gmelin) View in Reaxys

–O

2 Na +

Rx-ID: 26166271 View in Reaxys 394/501 Yield

Conditions & References in neat (no solvent), decompn. in vacuum over H2SO4 and K with formation of acetic anhydride; Franzen; Ber.; vol. 41; (1908); p. 3642 - 3642 ; (from Gmelin) View in Reaxys in neat (no solvent), decompn. in vacuum over H2SO4 and K with formation of acetic anhydride; vol. Na: MVol.; 314, page 860 - 863 ; (from Gmelin) View in Reaxys

–O

Na +

Rx-ID: 692572 View in Reaxys 395/501 Yield

Conditions & References Gattermann; View in Reaxys Rousset; Bulletin de la Societe Chimique de France; vol. <3>13; (1895); p. 330 View in Reaxys Tassinari; Chemische Berichte; vol. 11; (1878); p. 2031 View in Reaxys Henle; Justus Liebigs Annalen der Chemie; vol. 348; (1906); p. 29 View in Reaxys

129/149

2016-05-09 22:47:20

N H

N Cl

Rx-ID: 5818303 View in Reaxys 396/501 Yield

Conditions & References Eckstein; Chemische Berichte; vol. 39; (1906); p. 2136 View in Reaxys

H N

H N O

Rx-ID: 6082294 View in Reaxys 397/501 Yield

Conditions & References T= 20 °C , analog verlaeuft die Reaktion mit Phenylessigsaeure Dieckmann; Breest; Chemische Berichte; vol. 39; (1906); p. 3054 View in Reaxys

N2O3 Rx-ID: 7081799 View in Reaxys 398/501

Yield

Conditions & References Zersetzung bei Licht Francesconi; Cialdea; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5>12 II; (1903); p. 74; Gazzetta Chimica Italiana; vol. 34 I; (1904); p. 439 View in Reaxys

O O

<naphthol-(1)-ethyl ether >-sulfonic acid-(4) O

Rx-ID: 8267261 View in Reaxys 399/501 Yield

Conditions & References beim Liegen an der Luft Witt; Schneider; Chemische Berichte; vol. 34; (1901); p. 3172 View in Reaxys

O N

dimethylfurodiazole

N O

Rx-ID: 7074560 View in Reaxys 400/501 Yield

Conditions & References T= 300 - 350 °C Stolle; Chemische Berichte; vol. 32; (1899); p. 797; Journal fuer Praktische Chemie (Leipzig); vol. <2> 69; (1904); p. 150 View in Reaxys

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2016-05-09 22:47:20

O N

O O

Rx-ID: 513503 View in Reaxys 401/501 Yield

Conditions & References T= 200 °C Limpricht; Justus Liebigs Annalen der Chemie; vol. 299; (1898); p. 310; Justus Liebigs Annalen der Chemie; vol. 309; (1899); p. 113 View in Reaxys

lime/chalk/

calcium fluoride Rx-ID: 7070786 View in Reaxys 402/501

Yield

Conditions & References Meslans; Annales de Chimie (Cachan, France); vol. <7>1; (1894); p. 416 View in Reaxys O

–C

N+

HN O

Rx-ID: 264085 View in Reaxys 403/501 Yield

Conditions & References With acetic acid Nef; Justus Liebigs Annalen der Chemie; vol. 270; (1892); p. 281 View in Reaxys

O –C

H N

N+

HN O

Rx-ID: 639654 View in Reaxys 404/501 Yield

Conditions & References Nef; Justus Liebigs Annalen der Chemie; vol. 270; (1892); p. 281 View in Reaxys

–

Ag+

Rx-ID: 26113010 View in Reaxys 405/501 Yield 0%

Conditions & References in neat (no solvent), quantitaive decompn. in presence of H2O at 230-240°C; Kachler, J.; Monatshefte fuer Chemie; vol. 12; (1891); p. 338 - 349 View in Reaxys vol. Ag: MVol.B5; 2.2.7.2, page 125 - 126 ; (from Gmelin) View in Reaxys

131/149

2016-05-09 22:47:20

O O

N O O

Rx-ID: 431060 View in Reaxys 406/501 Yield

Conditions & References Mazzara; Gazzetta Chimica Italiana; vol. 20; (1890); p. 423 View in Reaxys

–

O Na +

Cl O

OH O

H 2N 2

sodium chloride Rx-ID: 6731339 View in Reaxys 407/501

Yield

Conditions & References Hentschel; Journal fuer Praktische Chemie (Leipzig); vol. <2>36; (1887); p. 103,314 View in Reaxys

N N

O O

Rx-ID: 398110 View in Reaxys 408/501 Yield

Conditions & References Erhitzen ueber den Schmelzpunkt Ponomarew; Chemische Berichte; vol. 18; (1885); p. 3267 View in Reaxys

lead nitrate Rx-ID: 5818075 View in Reaxys 409/501 Yield

Conditions & References Lachowicz; Chemische Berichte; vol. 17; (1884); p. 1283 View in Reaxys

O O O

bis-<α-butyroxyethyl>-ether Rx-ID: 7069614 View in Reaxys 410/501 Yield

Conditions & References T= 180 °C Geuther; Justus Liebigs Annalen der Chemie; vol. 226; (1884); p. 223 View in Reaxys O O

O O

aqueous alcoholic KOH-solution

132/149

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O HO

OH O

Rx-ID: 7054820 View in Reaxys 411/501 Yield

Conditions & References unterwirft man daher die erh. freien Saeuren der Dest., so geht unter Kohlendioxyd-Entwicklung das Anhydrid der Aethylidendiessigsaeure ueber Komnenos; Justus Liebigs Annalen der Chemie; vol. 218; (1883); p. 166 View in Reaxys

–O

Ag+

Cl O

Rx-ID: 8258054 View in Reaxys 412/501 Yield

Conditions & References Krutwig; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1882); p. 816 View in Reaxys –O

Ag+ Cl

Rx-ID: 188426 View in Reaxys 413/501 Yield

Conditions & References Spring; Chemische Berichte; vol. 14; (1881); p. 758 View in Reaxys O–

O–

2 Ag+

Rx-ID: 692619 View in Reaxys 414/501 Yield

Conditions & References Nowaschin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 13; (1881); p. 241 View in Reaxys

O O

Rx-ID: 422563 View in Reaxys 415/501 Yield

Conditions & References Zerfaellt bei der Destillation Barbier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 90; (1880); p. 37; Bulletin de la Societe Chimique de France; vol. <2>33; (1880); p. 55 View in Reaxys O

stilbene (?) Cl

Rx-ID: 6219950 View in Reaxys 416/501 Yield

Conditions & References Perkin; Hodgkinson; Journal of the Chemical Society; vol. 37; (1880); p. 726 View in Reaxys

133/149

2016-05-09 22:47:20

bromide of/the/ bromoacetic acid

Br O

Rx-ID: 6680225 View in Reaxys 417/501 Yield

Conditions & References With sodium acetate, Destillation des entstandenen gemischtes Anhydrids Naumann; Justus Liebigs Annalen der Chemie; vol. 129; (1864); p. 268 View in Reaxys Gal; ; (1870); p. 597 View in Reaxys O

N H

Rx-ID: 639663 View in Reaxys 418/501 Yield

Conditions & References Gautier; Annales de Chimie (Cachan, France); vol. <4>17; (1869); p. 222; Justus Liebigs Annalen der Chemie; vol. 151; (1869); p. 240 View in Reaxys O

N H

Rx-ID: 639742 View in Reaxys 419/501 Yield

Conditions & References Gautier; Annales de Chimie (Cachan, France); vol. <4>17; (1869); p. 222; Justus Liebigs Annalen der Chemie; vol. 151; (1869); p. 240 View in Reaxys

–O

Pb4+

Rx-ID: 534728 View in Reaxys 420/501 Yield

Conditions & References With carbon disulfide, T= 165 °C Broughton; ; (1865); p. 306 View in Reaxys

–O

O Na +

poly glycolide

sodium bromide

Rx-ID: 6219735 View in Reaxys 421/501 Yield

Conditions & References T= 160 °C Naumann; Justus Liebigs Annalen der Chemie; vol. 129; (1864); p. 268 View in Reaxys

–O

K+

Rx-ID: 534619 View in Reaxys 422/501 Yield

Conditions & References With trichlorophosphate Gerhardt; Annales de Chimie (Cachan, France); vol. <3> 37; (1853); p. 300; Justus Liebigs Annalen der Chemie; vol. 87; (1853); p. 73 View in Reaxys With phosphorus trichoride

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2016-05-09 22:47:20

Gerhardt; Annales de Chimie (Cachan, France); vol. <3> 37; (1853); p. 300; Justus Liebigs Annalen der Chemie; vol. 87; (1853); p. 73 View in Reaxys –O

K+

Rx-ID: 692570 View in Reaxys 423/501 Yield

Conditions & References Gerhardt; Annales de Chimie (Cachan, France); vol. <3> 37; (1853); p. 300; Justus Liebigs Annalen der Chemie; vol. 87; (1853); p. 73 View in Reaxys

–O

O Na +

Ca 2+

Rx-ID: 534668 View in Reaxys 424/501 Yield

Conditions & References With tetrachloromethane, phosgene, sulfur trioxide, Reagens 4: Schwefelsaeurechlorid Patent; Beatty; DE290702; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 79 View in Reaxys With sulfuryl dichloride, sulfur trioxide Patent; Chem.Fabr.v.Heyden; DE358774; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 13; p. 1116 View in Reaxys With sulfuryl dichloride Patent; Verein f. chem. Ind.; DE161882 View in Reaxys

–O

Ca 2+

Rx-ID: 538613 View in Reaxys 425/501 Yield

Conditions & References With α,α,α-trichlorotoluene, T= 170 - 180 °C Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With α,α,α-trichlorotoluene, T= 230 - 240 °C , im Rohr Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With acetic acid, α,α,α-trichlorotoluene, unter Rueckfluss Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With acetic anhydride, α,α,α-trichlorotoluene, unter Rueckfluss Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With α,α,α-trichlorotoluene, toluene, unter Rueckfluss Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys With sulfuryl dichloride, sulfur trioxide, acetic anhydride Patent; Chem.Fabr.v.Heyden; DE358774; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 13; p. 1116

135/149

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View in Reaxys With chlorosulfonic acid Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With chlorosulfonic acid, sulfuryl dichloride Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With chlorosulfonic acid, sulphur pentoxydichloride Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With disulfur dichloride, chlorosulfonic acid Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys With tetrachloromethane, phosgene, sulfur trioxide, Reagens 4: Schwefelsaeurechlorid Patent; Beatty; DE290702; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 79 View in Reaxys With chlorosulfonic acid, sulfur trioxide Patent; Chem.Fabr.v.Heyden; DE372716; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 253 View in Reaxys

H N

NH 2

Rx-ID: 639532 View in Reaxys 426/501 Yield

Conditions & References Patent; Usines du Rhone; DE451533; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 128 View in Reaxys

Cl Cl

Rx-ID: 666320 View in Reaxys 427/501 Yield

Conditions & References With sodium acetate, T= 170 - 180 °C , unter Rueckfluss Patent; Wacker,A.; DE368340; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 251 View in Reaxys

–O

O Na +

S Cl

Rx-ID: 730093 View in Reaxys 428/501 Yield

Conditions & References Patent; Chem.Fabr.v.Heyden; DE123052; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 6; p. 35 View in Reaxys O

acetate of di-valent metal Rx-ID: 5589280 View in Reaxys 429/501 Yield

Conditions & References With sulfuryl dichloride

136/149

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Patent; Verein f. chem. Ind.; DE161882 View in Reaxys Patent; Verein f. chem. Ind.; DE63593; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 3; p. 8 View in Reaxys O

acetate of mono-valent metal Rx-ID: 5589281 View in Reaxys 430/501 Yield

Conditions & References With sulfuryl dichloride Patent; Verein f. chem. Ind.; DE161882 View in Reaxys Patent; Verein f. chem. Ind.; DE63593; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 3; p. 8 View in Reaxys O

acetate Rx-ID: 5589282 View in Reaxys 431/501 Yield

Conditions & References With chlorine, anhydrous sulfurous acid Patent; Bayer and Co.; DE127350 View in Reaxys With silicon tetrafluoride Patent; Sommer; DE171146 View in Reaxys With sulphur monochloride, im Vakuum Patent; Kessler; DE132605 View in Reaxys O

alkali cetate Rx-ID: 5589284 View in Reaxys 432/501 Yield

Conditions & References With trichlorophosphate Patent; Verein f. chem. Ind.; DE163103 View in Reaxys With phosgene Patent; Verein f. chem. Ind.; DE163103 View in Reaxys O

alkaline earth acetate Rx-ID: 5589285 View in Reaxys 433/501 Yield

Conditions & References With trichlorophosphate Patent; Verein f. chem. Ind.; DE163103 View in Reaxys With phosgene

137/149

2016-05-09 22:47:20

Patent; Verein f. chem. Ind.; DE163103 View in Reaxys With sulfuryl dichloride, alkali salt Patent; Verein f. chem. Ind.; DE171787 View in Reaxys With alkali salt, trichlorophosphate Patent; Verein f. chem. Ind.; DE171787 View in Reaxys With phosgene, alkali salt Patent; Verein f. chem. Ind.; DE171787 View in Reaxys With alkali salt, chlorine, anhydrous sulfurous acid Patent; Verein f. chem. Ind.; DE171787 View in Reaxys O

alkali cetate

alkaline earth acetate Rx-ID: 5589286 View in Reaxys 434/501

Yield

Conditions & References With sulfur dioxide, chlorine Patent; Verein f. chem. Ind.; DE167304 View in Reaxys O

compound of sulfur dioxide with acetate salt Rx-ID: 5589288 View in Reaxys 435/501 Yield

Conditions & References With chlorine Patent; Hoechster Farbw.; DE210805 View in Reaxys

acetaldehyde and paraldehyde Rx-ID: 5724464 View in Reaxys 436/501 Yield

Conditions & References With sulfuric acid, T= 70 - 80 °C , p= 100Torr , bei der Destillation Patent; Usines du Rhone; DE346236; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 13; p. 1085 View in Reaxys O

ethylene diacetate

acetaldehyde and paraldehyde Rx-ID: 5724465 View in Reaxys 437/501

Yield

Conditions & References With sulfuric acid, bei der Destillation Patent; Konsort.f.elektrochem.Ind.; DE391674; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 222 View in Reaxys With phosphoric acid, bei der Destillation

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Patent; Shawinigan Water and Power Co.; DE408416; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 203 View in Reaxys With zinc, bei der Destillation Patent; Bayer and Co.; DE360325; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 250 View in Reaxys With zinc(II) chloride Patent; Usines du Rhone; DE451533; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 128 View in Reaxys With zinc dibromide Patent; Usines du Rhone; DE451533; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 128 View in Reaxys With acetic acid, zinc Patent; Usines du Rhone; DE451533; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 128 View in Reaxys –O

Na +

acetic acid and ethylidene diacetate Rx-ID: 5724510 View in Reaxys 438/501

Yield

Conditions & References With chlorine, T= 10 - 12 °C Patent; Wacker,A.; DE372528; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 252 View in Reaxys

O O

sodium acetate (excess)

S Cl

Rx-ID: 5818080 View in Reaxys 439/501 Yield

Conditions & References Patent; Chem.Fabr.v.Heyden; DE123052 View in Reaxys

–O

O Na +

Rx-ID: 5853519 View in Reaxys 440/501 Yield

Conditions & References T= 10 - 12 °C Patent; Wacker,A.; DE372528; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 252 View in Reaxys

silicon tetrachloride Rx-ID: 5929161 View in Reaxys 441/501 Yield

Conditions & References Patent; Konsort. fuer elektrochem. Ind.; DE394730; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 255 View in Reaxys

139/149

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OH HO

P OH O

Rx-ID: 7058107 View in Reaxys 442/501 Yield

Conditions & References bei der Destillation Patent; Shawinigan Water and Power Co.; DE408416; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 203 View in Reaxys

OH HO

S OO

Rx-ID: 7058108 View in Reaxys 443/501 Yield

Conditions & References Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys bei der Destillation Patent; Konsort.f.elektrochem.Ind.; DE391674; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 222 View in Reaxys

(v1)

-2

Hg 2+ (v1)

S OO

Rx-ID: 7058109 View in Reaxys 444/501 Yield

Conditions & References Patent; Bosnische Elektrizitaets-A.-G.; DE284996; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 12; p. 76 View in Reaxys

zinc bromide

Rx-ID: 7058111 View in Reaxys 445/501 Yield

Conditions & References Patent; Usines du Rhone; DE451533; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 128 View in Reaxys

zinc

Rx-ID: 7058112 View in Reaxys 446/501 Yield

Conditions & References bei der Destillation Patent; Bayer and Co.; DE360325; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 250 View in Reaxys

zinc

Rx-ID: 7058113 View in Reaxys 447/501 Yield

Conditions & References Patent; Usines du Rhone; DE451533; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 128 View in Reaxys

140/149

2016-05-09 22:47:20

OH HO

S OO

Rx-ID: 7065197 View in Reaxys 448/501 Yield

Conditions & References T= 70 - 80 °C , p= 100Torr , bei der Destillation Patent; Usines du Rhone; DE346236; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 13; p. 1085 View in Reaxys

–O

Zn 2+

Rx-ID: 8236294 View in Reaxys 449/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Hg 2+

Rx-ID: 8236295 View in Reaxys 450/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Li+

Rx-ID: 8236296 View in Reaxys 451/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Rb +

Rx-ID: 8236297 View in Reaxys 452/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

K+

Rx-ID: 8236298 View in Reaxys 453/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–

Ag+

Rx-ID: 8236299 View in Reaxys 454/501

141/149

2016-05-09 22:47:20

Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Cu 2+

Rx-ID: 8236300 View in Reaxys 455/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–

Na +

Rx-ID: 8236301 View in Reaxys 456/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Sr2+

Rx-ID: 8236302 View in Reaxys 457/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

Al3+– O 3

Rx-ID: 8236303 View in Reaxys 458/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Cu +

Rx-ID: 8236304 View in Reaxys 459/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Cl 2

O (v1)

O +Hg

Hg +

(v1)

Rx-ID: 8236305 View in Reaxys 460/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

142/149

2016-05-09 22:47:20

1 –

Cl (v4)

H 3N

(v2)

Ag NH 3

(v4)

Rx-ID: 8236306 View in Reaxys 461/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

O Hg 2+

O HgS

Rx-ID: 8236307 View in Reaxys 462/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

O Cu 2+

Rx-ID: 8236308 View in Reaxys 463/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

O Cu 2+

Rx-ID: 8236309 View in Reaxys 464/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

4 H

Sr2+

Rx-ID: 8236310 View in Reaxys 465/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

S O

–O

O Cu 2+

Cl 4

Rx-ID: 8236311 View in Reaxys 466/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

143/149

2016-05-09 22:47:20

–O

3 H

Na +

Rx-ID: 8236312 View in Reaxys 467/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

2 Sr2+

Rx-ID: 8236313 View in Reaxys 468/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Zn 2+

Rx-ID: 8236314 View in Reaxys 469/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

5 H

H O

Zn 2+

Rx-ID: 8236315 View in Reaxys 470/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

(v2)

Rx-ID: 8236316 View in Reaxys 471/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys –

S O

O Cu 2+

-1 (v2)

(v2)

(v4)

Rx-ID: 8236317 View in Reaxys 472/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

144/149

2016-05-09 22:47:20

Al3+

(v1)

–O

O -1 H2 H

–O

O O

Rx-ID: 8236318 View in Reaxys 473/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–

Na +

silicon oxy chloride/s Rx-ID: 8236324 View in Reaxys 474/501

Yield

Conditions & References Zanetti; Journal of the American Chemical Society; vol. 34; p. 1599 View in Reaxys

–O

Zn 2+

sulfur Rx-ID: 8236326 View in Reaxys 475/501

Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Hg 2+

sulfur Rx-ID: 8236327 View in Reaxys 476/501

Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Li+

sulfur Rx-ID: 8236328 View in Reaxys 477/501

Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Rb +

sulfur Rx-ID: 8236329 View in Reaxys 478/501

Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

O K+

sulfur Rx-ID: 8236330 View in Reaxys 479/501

Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191

145/149

2016-05-09 22:47:20

View in Reaxys –O

Ag+

sulfur

Rx-ID: 8236331 View in Reaxys 480/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Cu 2+

sulfur

Rx-ID: 8236332 View in Reaxys 481/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Na +

sulfur

Rx-ID: 8236333 View in Reaxys 482/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Sr2+

sulfur

Rx-ID: 8236334 View in Reaxys 483/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

Al3+– O 3

sulfur

Rx-ID: 8236335 View in Reaxys 484/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Cu +

sulfur

Rx-ID: 8236336 View in Reaxys 485/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

O (v1)

O +Hg

Hg +

(v1)

sulfur Rx-ID: 8236337 View in Reaxys 486/501

146/149

2016-05-09 22:47:20

Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

(v4)

H 3N

1 – O

(v2)

Ag NH 3

(v4)

sulfur

Rx-ID: 8236338 View in Reaxys 487/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

O Hg 2+

sulfur

HgS

Rx-ID: 8236339 View in Reaxys 488/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

O Cu 2+

sulfur

Rx-ID: 8236340 View in Reaxys 489/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

O Cu 2+

Cl H

sulfur

Rx-ID: 8236341 View in Reaxys 490/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

4 H

sulfur

Sr2+

Rx-ID: 8236342 View in Reaxys 491/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

147/149

2016-05-09 22:47:20

–O

O Cu 2+

sulfur

Rx-ID: 8236343 View in Reaxys 492/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

3 H

sulfur

Na +

Rx-ID: 8236344 View in Reaxys 493/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

sulfur

2 Sr2+

Rx-ID: 8236345 View in Reaxys 494/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

sulfur

Zn 2+

Rx-ID: 8236346 View in Reaxys 495/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

5 H

H O

sulfur

Zn 2+

Rx-ID: 8236347 View in Reaxys 496/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

(v2)

sulfur

Rx-ID: 8236348 View in Reaxys 497/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

148/149

2016-05-09 22:47:20

–O

O Cu 2+

-1 (v2)

sulfur

(v2)

(v4)

Rx-ID: 8236349 View in Reaxys 498/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys –

Al3+

–

O O

Cl (v1)

O -1 H2 H

sulfur

Rx-ID: 8236350 View in Reaxys 499/501 Yield

Conditions & References Patent; Naamlooze Vennootschap Fabriek van chemische Producten Schiedam; DE275846; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 1191 View in Reaxys

–O

Ag+

Ag2S

Rx-ID: 26113024 View in Reaxys 500/501 Yield

Conditions & References

>99

in acetic anhydride, on heating for a longer period of time; vol. Ag: MVol.B5; 2.2.7.5, page 127 - 128 ; (from Gmelin) View in Reaxys O– O

NH +4

–O 2 NH + 4

O–

Rx-ID: 26409821 View in Reaxys 501/501 Yield

Conditions & References in sulfur dioxide, solvolysis of CH3COONH4 in liquid SO2 at 70 to 80°C (starting at -50°C) in a sealed tube;; decompn. of thionylacetate into SO2 and acetic anhydride; vol. S: MVol.B1; 146, page 319 - 322 View in Reaxys Behne, W.; Diss. Greifswald 1945 laut Jander, G., Die Grundlagen der Chemie in fluessigem Schwefeldioxyd in: Naturw. 26 (1938) 264/73 ; (from Gmelin) View in Reaxys

149/149

2016-05-09 22:47:20