4-Hydroxy-3,5-dimethoxybenzaldehyde (Syringaldehyde) by Asch

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Reactions (87)

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Targets (306)

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Citations (105)

References

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Rx-ID: 152746 Find similar reactions

With sodium hydroxide; chloroform

Graebe; Martz

Chemische Berichte, 1903 , vol. 36, p. 1033 Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: zinc chloride; urea; glacial acetic acid 2: durch aufeinanderfolgende Verseifung und Oxydation mit Kupfersulfat 3: dimethyl-p-toluidine View Scheme

Mauthner

Justus Liebigs Annalen der Chemie, 1913 , vol. 395, p. 279 Full Text Show Details

Multi-step reaction with 2 steps 1: potassium carbonate View Scheme

Pauly; Strassberger

Chemische Berichte, 1929 , vol. 62, p. 2279 Full Text Show Details

Multi-step reaction with 2 steps 1: potassium carbonate View Scheme

Pauly; Strassberger

Chemische Berichte, 1929 , vol. 62, p. 2279 Full Text Show Details

Multi-step reaction with 2 steps 1: (i) aq. NaOH, (ii) /BRN= 1209228/, As2O3, aq. NaOH 2: O2, CuCl / dimethylsulfoxide View Scheme

Claus,P. et al.

Monatshefte fuer Chemie, 1972 , vol. 103, p. 1178 - 1193 Full Text View citing articles Show Details

Synthesize Find similar With chloroform; sodium methylate

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Rx-ID: 296739 Find similar reactions

Freudenberg; Huebner

Chemische Berichte, 1952 , vol. 85, p. 1181,1188 Full Text View citing articles Show Details

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Rx-ID: 300739 Find similar reactions

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With boric acid; glycerol

T=150 - 160°C; Erhitzen des Reaktionsgemisches mit wss.H2SO4;

Allen; Leubner

Org.Synth.Coll.Vol., 1963 , vol. IV, p. 866 Full Text Show Details

Manske; Ledingham; Holmes

Canadian Journal of Research, Section B: Chemical Sciences, 1945 , vol. 23, p. 100,102 Full Text View citing articles Show Details

With trifluoroacetic acid

Heating;

Diana, Guy D.; Cutcliffe, David; Oglesby, Richard C.; Otto, Michael J.; Mallamo, John P.; et al.

Journal of Medicinal Chemistry, 1989 , vol. 32, # 2 p. 450 - 455 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With methanol; sodium methylate; copper

unter Druck;

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Rx-ID: 310191 Find similar reactions

Pearl

Journal of Organic Chemistry, 1957 , vol. 22, p. 1229,1231 Full Text View citing articles Show Details

Pepper; MacDonald

Canadian Journal of Chemistry, 1953 , vol. 31, p. 476,483 Full Text Show Details

Synthesize Find similar With sodium hydroxide; nitrobenzene

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Rx-ID: 322714 Find similar reactions

Pearl

Journal of the American Chemical Society, 1948 , vol. 70, p. 1746 Full Text View citing articles Show Details

Synthesize Find similar With hydrogenchloride; diethyl ether; tin(ll) chloride

Reagens 4:Chloroform;Erwaermen des Reaktionsprodukts mit Wasser;

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Rx-ID: 379907 Find similar reactions

McCord

Journal of the American Chemical Society, 1931 , vol. 53, p. 4181 Full Text View citing articles Show Details

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Rx-ID: 486656 Find similar reactions

Pauly; Strassberger

Chemische Berichte, 1929 , vol. 62, p. 2279 Full Text Show Details

Synthesize Find similar With 2,3,4-trimethylaniline

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Rx-ID: 487606 Find similar reactions

Mauthner

Justus Liebigs Annalen der Chemie, 1913 , vol. 395, p. 279 Full Text Show Details

Synthesize Find similar With sodium hydroxide; ethanol; hydrogen

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Rx-ID: 493926 Find similar reactions

Mauthner

Journal fuer Praktische Chemie (Leipzig), 1935 , vol. <2> 142, p. 26,31 Full Text View citing articles Show Details

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Rx-ID: 496776 Find similar reactions

With Pd-BaSO4; xylene

T=150 - 160°C; Hydrogenation;

Imaki et al.

Nippon Nogei Kagaku Kaishi, 1944 , vol. 20, p. 289,292 Chem.Abstr., 1949 , p. 1743 Full Text Show Details

Multi-step reaction with 2 steps 1: palladium/BaSO4; xylene / Hydrogenation 2: CHCl3; methanol. sodium methylate View Scheme

Freudenberg; Huebner

Chemische Berichte, 1952 , vol. 85, p. 1181,1188 Full Text View citing articles Show Details

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Rx-ID: 590499 Find similar reactions

95%

With aluminum (III) chloride in dichloromethane

T=20°C; 12 h; Inert atmosphere;

Shirali, Anupama; Sriram, Madhavi; Hall, John J.; Nguyen, Benson L.; Guddneppanavar, Rajsekhar; Hadimani, Mallinath B.; Ackley, J. Freeland; Siles, Rogelio; Jelinek, Christopher J.; Arthasery, Phyllis; Brown, Rodney C.; Murrell, Victor Leon; McMordie, Austin; Sharma, Suman; Chaplin, David J.; Pinney, Kevin G.

Journal of Natural Products, 2009 , vol. 72, # 3 p. 414 - 421 Title/Abstract Full Text View citing articles Show Details

92%

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; thiophenol in toluene

Heating;

Zou, Hong Bin; Dong, Sheng Yi; Zhou, Chang Xin; Hu, Li Hong; Wu, Yi Hang; Li, Hai Bo; Gong, Jing Xu; Sun, Lian Li; Wu, Xiu Mei; Bai, Hua; Fan, Bo Tao; Hao, Xiao Jiang; Stoeckigt, Joachim; Zhao, Yu

Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 6 p. 2060 - 2071 Title/Abstract Full Text View citing articles Show Details

92%

With magnesium iodide

T=80°C; 0.5 h; neat (no solvent);

Bao, Kai; Fan, Aixue; Dai, Yi; Zhang, Liang; Zhang, Weige; Cheng, Maosheng; Yao, Xinsheng

Organic and Biomolecular Chemistry, 2009 , vol. 7, # 24 p. 5084 - 5090 Title/Abstract Full Text View citing articles Show Details

80%

With piperidine; water

48 h; Heating;

Ren, Xinfeng; Chen, Xiaochuan; Peng, Kun; Xie, Xingang; Xia, Yamu; Pan, Xinfu

Tetrahedron Asymmetry, 2002 , vol. 13, # 16 p. 1799 - 1804 Title/Abstract Full Text View citing articles Show Details

80%

With piperidine in water

48 h; Heating;

Su, Ying; Ren, Xin-Feng; She, Xue-Gong; Pan, Xin-Fu

Journal of the Chinese Chemical Society, 2004 , vol. 51, # 6 p. 1333 - 1337 Title/Abstract Full Text View citing articles Show Details

78%

With 1-N-ferrocenylmethyl benzimidazole tagged polymer in N,N-dimethyl-formamide

Reflux; Hide Experimental Procedure

Kurane, Rajanikant; Gaikwad, Vipul; Jadhav, Jagannath; Salunkhe, Rajashri; Rashinkar, Gajanan

Tetrahedron Letters, 2012 , vol. 53, # 47 p. 6361 - 6366,6 Title/Abstract Full Text Show Details

Typical procedure for O-demethylation

General procedure: A mixture of aryl methyl ether (1 mmol) and [FemMerBenz]Al2Cl7 (200 mg, 0.96 mol percent) in DMF (5 mL) was refluxed in an oil bath. After completion of the reaction as monitored by the TLC, the reaction mixture was cooled and filtered. The filtrate was poured into water (20 mL) and extracted with ethyl acetate (3 20 mL). The combined organic layers were dried over Na2SO4. Evaporation of the solvent followed by column chromatography over silica gel using ethyl acetate/ petroleum ether (1:4 v/v) afforded pure O-demethylated product, which was characterized by spectral methods. 74%

With piperidine in water

48 h; Reflux;

Pettit, George R.; Melody, Noeleen; Thornhill, Andrew; Knight, John C.; Groy, Thomas L.; Herald, Cherry L.

Journal of Natural Products, 2009 , vol. 72, # 9 p. 1637 - 1642 Title/Abstract Full Text View citing articles Show Details

72%

With dimethyl amine in water

T=140°C; P=7500.75 Torr; 18 h; Autoclave; Hide Experimental Procedure

BASF SE

Patent: US2011/245544 A1, 2011 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details

EXAMPLE 3A 100 ml glass autoclave is charged with 11.8 g (60.0 mmol) of 3,4,5-trimethoxybenzaldehyde and 47.2 g (420 mmol) of dimethylamine (40percent solution in water). The autoclave is closed and the biphasic reaction mixture is stirred at 140° C. (autogenous pressure 10 bar) for 18 h. Excess dimethylamine and water are removed under reduced pressure, methyl tert-butyl ether is added and the mixture is acidified with 30percent hydrochloric acid in water. After phase separation and removal of all volatile constituents of the organic phase, 4-hydroxy-3,5-dimethoxybenzaldehyde is obtained in a yield of 72percent. 72%

With piperidine; water

48 h; Reflux;

Ding, Junwei; Qi, Rongwei; Zhou, Haitang; Jiao, Bin; Xia, Yamu

Journal of Chemical Research, 2011 , vol. 35, # 9 p. 519 - 521 Title/Abstract Full Text View citing articles Show Details

72%

With dimethyl amine in water

T=140°C; P=7500.75 Torr; 18 h; Autoclave; Hide Experimental Procedure

BASF SE; EBEL, KLAUS; RUDENAUER, STEFAN

Patent: JP5816260 B2, 2015 ; Location in patent: Paragraph 0048 ; Title/Abstract Full Text Show Details

In a 100 ml glass autoclave are 1 1, 8 g (60.0 mmol) of 3,4,5-trimethoxy and 47.2 g (420 mmol) dimethylamine (40percent solution in water) filled.The autoclave is closed and stirred at 140 ° C (self-pressure 10 bar), the biphasic reaction mixture for 18 h.Excess dimethylamine and water are removed under reduced pressure, methyl tert added and asked the mixture with 30percent hydrochloric acid in water.After phase separation and removal of all volatile components of the organic phase, 4-hydroxy-3,5-dimethoxybenzaldehyde in a yield of 72percent. 65%

With piperidine in water

20 h; Heating;

Rizzacasa, Mark A.; Sargent, Melvyn V.

Australian Journal of Chemistry, 1987 , vol. 40, # 10 p. 1737 - 1743 Title/Abstract Full Text Show Details

With sulfuric acid

T=40°C;

Sharp

Journal of the Chemical Society, 1937 , p. 852 Full Text Show Details

With sulfuric acid

T=40°C; 8 h;

MERCK PATENT GESELLSCHAFT MIT BESCHRAENKTER HAFTUNG

Patent: JP2005/522479 A, 2005 ; Location in patent: Page/Page column 13 ; Title/Abstract Full Text Show Details

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Rx-ID: 753924 Find similar reactions

With sodium hydroxide

Kratzl; Billek

Holzforschung, 1953 , vol. 7, p. 66,69 Full Text View citing articles Show Details

Kratzl et al.

Monatshefte fuer Chemie, 1954 , vol. 85, p. 1154,1160 Full Text View citing articles Show Details

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Rx-ID: 796047 Find similar reactions

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Mauthner

Justus Liebigs Annalen der Chemie, 1913 , vol. 395, p. 279 Full Text Show Details

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Rx-ID: 1992884 Find similar reactions

96%

With copper diacetate; ethylene glycol

T=50°C; 8 h; Green chemistry; chemoselective reaction;

Jiang, Jian-An; Chen, Cheng; Huang, Jian-Gang; Liu, Hong-Wei; Cao, Song; Ji, Ya-Fei

Green Chemistry, 2014 , vol. 16, # 3 p. 1248 - 1254 Title/Abstract Full Text View citing articles Show Details

90%

With 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; copper diacetate in water; acetonitrile

T=20°C; 3 h; Green chemistry; Hide Experimental Procedure

Jiang, Jian-An; Du, Jia-Lei; Wang, Zhan-Guo; Zhang, Zhong-Nan; Xu, Xi; Zheng, Gan-Lin; Ji, Ya-Fei

Tetrahedron Letters, 2014 , vol. 55, # 10 p. 1677 - 1681 Title/Abstract Full Text View citing articles Show Details

General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)2 (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH3CN/H2O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product. 86%

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane

16 h; Ambient temperature;

Becker, Hans-Dieter; Bjoerk, Anders; Adler, Erich

Journal of Organic Chemistry, 1980 , vol. 45, # 9 p. 1596 - 1600 Title/Abstract Full Text View citing articles Show Details

63%

With nitric acid; sodium nitrite in acetonitrile

Bozell, Joseph J.; Hoberg, John O.; Dimmel, Donald R.

Tetrahedron Letters, 1998 , vol. 39, # 16 p. 2261 - 2264 Title/Abstract Full Text View citing articles Show Details

With oxygen; copper(l) chloride in dimethyl sulfoxide

Claus,P. et al.

Monatshefte fuer Chemie, 1972 , vol. 103, p. 1178 - 1193 Full Text View citing articles Show Details

With pyridinium chlorochromate

Kang, Tae-Souk; Jo, Hyang-Ok; Park, Woo-Kyu; Kim, Jong-Pyung; Konishi, Yasuo; Kong, Jae-Yang; Park, No-Sang; Jung, Young-Sik

Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 5 p. 1663 - 1667 Title/Abstract Full Text View citing articles Show Details

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B: 99%

With cupric(II) carbonate; copper (II) hydroxide in methanol

T=125°C; 3 h; var. time; also without CO2, other aromatic bromides; MechanismProduct distribution;

Nobel, D.

Journal of the Chemical Society, Chemical Communications, 1993 , # 4 p. 419 - 420 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2040581 Find similar reactions

98%

With methanol; Methyl formate; copper(l) chloride

T=115°C; 2 h; AutoclaveGreen chemistry; Hide Experimental Procedure

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Guo, Ying; Ji, Si-Zhe; Chen, Cheng; Liu, Hong-Wei; Zhao, Jian-Hong; Zheng, Yu-Lin; Ji, Ya-Fei

Research on Chemical Intermediates, 2015 , vol. 41, # 11 p. 8651 - 8664 Title/Abstract Full Text View citing articles Show Details

Typical procedure for synthesis of 1 (Table 1)

General procedure: A Teflon-lined autoclave (25 mL) was charged with MeONa (1.08 g, 20.0 mmol), MeOH (10 mL), CuCl (40 mg, 0.40 mmol), HCOOMe (0.25 mL, 0.97 g/mL, 4.0 mmol), and monohaloarene (10.0 mmol) then heated to 115 °C, with stirring, for 2 h. After completion of the reaction, the reactor was cooled to room temperature. The mixture was stirred for 0.5 h in the open, then concentrated to recover pure MeOH. Diethyl ether (15 mL) and dilute hydrochloric acid (1.6 M, 15 mL) were added to the residue. The mixture separated into two layers, and the aqueous phase was extracted with diethyl ether (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography on silica gel (mobile phase: petroleum ether–ethyl acetate 15:1) to furnish 1 (conversion and selectivity were determined by GC–MS analysis). The purity of the recovered MeOH was measured as more than 99 percent by GC, and the water content of the recovered MeOH was measured as less than 0.12 percent by use of the Karl Fischer method. 92%

With copper(I) bromide in DMFA

Zabinski, Jerzy; Wolska, Irena; Maciejewska, Dorota

Journal of Molecular Structure, 2007 , vol. 833, # 1-3 p. 74 - 81 Title/Abstract Full Text View citing articles Show Details

88%

With Cu2Cl2 in DMFA

T=97°C; 2.5 h;

Manchand, Percy S.; Belica, Peter S.; Wong, Harry S.

Synthetic Communications, 1990 , vol. 20, # 17 p. 2659 - 2666 Title/Abstract Full Text Show Details

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99%

With copper(II) carbonate; copper(II) hydroxide; carbon dioxide in methanol

T=125°C; 3 h;

Nobel, D.

Journal of the Chemical Society, Chemical Communications, 1993 , # 4 p. 419 - 420 Title/Abstract Full Text View citing articles Show Details

95%

With ethyl acetate; copper(I) bromide in methanol

14 h; Heating;

Capdevielle, Patrice; Maumy, Michel

Tetrahedron Letters, 1993 , vol. 34, # 6 p. 1007 - 1010 Title/Abstract Full Text View citing articles Show Details

91%

With copper(I) chloride in N,N-dimethyl-formamide

T=97°C; 2.5 h;

Manchand, Percy S.; Belica, Peter S.; Wong, Harry S.

Synthetic Communications, 1990 , vol. 20, # 17 p. 2659 - 2666 Title/Abstract Full Text Show Details

90%

With copper(l) chloride in N,N-dimethyl-formamide

Li, Yan; Dai, Fang; Jin, Xiao-Ling; Ma, Meng-Meng; Wang, Yi-Hua; Ren, Xiao-Rong; Zhou, Bo

Food Chemistry, 2014 , vol. 158, p. 41 - 47 Title/Abstract Full Text View citing articles Show Details

83%

With copper dichloride in methanol; N,N-dimethyl-formamide

T=100°C; 1 h;

Rao, Durvasula V.; Stuber, F. A.

Synthesis, 1983 , # 4 p. 308 Title/Abstract Full Text Show Details

18 g

With copper dichloride in N,N-dimethyl-formamide

T=120°C; 1 h;

Puri, S. C.; Anand, S. M.; Atal, C. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985 , vol. 24, p. 294 - 295 Title/Abstract Full Text Show Details

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With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide in cyclohexane

6 h; other reaction time, other molar ratios of educt/AlI3 and educt/catalyst; Product distribution;

Andersson, Sven

Synthesis, 1985 , # 4 p. 437 - 439 Title/Abstract Full Text Show Details

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A: 90% B: 6 % Spectr.

With oxygen; (pyridine)lt;bis(salicylidene)ethylenediaminegt;cobalt in methanol

P=2585.7 Torr; Ambient temperature;

Bozell, Joseph J.; Hames, Bonnie R.; Dimmel, Donald R.

Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2398 - 2404 Title/Abstract Full Text View citing articles Show Details

A: 75% B: 19%

With C38H57CoN3O2; oxygen in methanol

T=0°C; Inert atmosphere; Reagent/catalystConcentrationTemperature;

Biannic, Berenger; Bozell, Joseph J.

Organic Letters, 2013 , vol. 15, # 11 p. 2730 - 2733 Title/Abstract Full Text View citing articles Show Details

A: 67% B: 25%

With C45H72CoN4O2; oxygen in methanol

T=20°C; P=2585.81 Torr; 16 h; Reagent/catalyst;

Biannic, Berenger; Bozell, Joseph J.; Elder, Thomas

Green Chemistry, 2014 , vol. 16, # 7 p. 3635 - 3642 Title/Abstract Full Text View citing articles Show Details

A: 11% B: 29%

With C37H56CoN4O2; oxygen in methanol

T=0°C; Inert atmosphere; ConcentrationReagent/catalystTime;

Biannic, Berenger; Bozell, Joseph J.

Organic Letters, 2013 , vol. 15, # 11 p. 2730 - 2733 Title/Abstract Full Text View citing articles Show Details

A: 28% B: 50 % Spectr.

With oxygen; cobalt-salen complex in methanol

P=2585.7 Torr; Ambient temperature;

Bozell, Joseph J.; Hames, Bonnie R.; Dimmel, Donald R.

Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2398 - 2404 Title/Abstract Full Text View citing articles Show Details

With Melanocarpus albomyces laccase; oxygen in 1,4-dioxane

24 h; sodium succinate buffer;

Maarit, Lahtinen; Kristiina, Kruus; Petri, Heinonen; Jussi, Sipilae

Journal of Agricultural and Food Chemistry, 2009 , vol. 57, # 18 p. 8357 - 8365 Title/Abstract Full Text View citing articles Show Details

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A: 17% B: 10 % Spectr.

With oxygen; lt;bislt; (salicylideneamino)ethylgt;aminegt;cobalt in methanol

P=2585.7 Torr; 24 h; Ambient temperature; Title compound not separated from byproducts;

Bozell, Joseph J.; Hames, Bonnie R.; Dimmel, Donald R.

Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2398 - 2404 Title/Abstract Full Text View citing articles Show Details

A: 17% B: 10 % Spectr.

With oxygen; lt;bislt; (salicylideneamino)ethylgt;aminegt;cobalt in methanol

P=2585.7 Torr; 24 h; Ambient temperature;

Bozell, Joseph J.; Hames, Bonnie R.; Dimmel, Donald R.

Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2398 - 2404 Title/Abstract Full Text View citing articles Show Details

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A: 11% B: 44 % Spectr.

With oxygen; lt;bislt; (salicylideneamino)ethylgt;aminegt;cobalt in methanol

P=2585.7 Torr; Ambient temperature; Title compound not separated from byproducts;

Bozell, Joseph J.; Hames, Bonnie R.; Dimmel, Donald R.

Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2398 - 2404 Title/Abstract Full Text View citing articles Show Details

A: 11% B: 45 % Spectr.

With oxygen; lt;bislt; (salicylideneamino)ethylgt;aminegt;cobalt in methanol

P=2585.7 Torr; 24 h; Ambient temperature;

Bozell, Joseph J.; Hames, Bonnie R.; Dimmel, Donald R.

Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2398 - 2404 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 4385830 Find similar reactions

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Kratzl,K.; Vierhapper,F.W.

Monatshefte fuer Chemie, 1971 , vol. 102, p. 425 - 430 Full Text View citing articles Show Details

(i) SnCl4, CH2Cl2, (ii) aq. HCl, HgCl2; Multistep reaction;

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98%

With chloro-trimethyl-silane; sodium iodide in water; acetonitrile

deprotection; 0.05 h;

Kamal, Ahmed; Ramana, K. Venkata; Arifuddin

Chemistry Letters, 1999 , # 8 p. 827 - 828 Title/Abstract Full Text View citing articles Show Details

92%

With triethylene diamine nickel thiosulfate; water in chloroform

Kamal; Arifuddin; Rao

Synlett, 2000 , # 10 p. 1482 - 1484 Title/Abstract Full Text View citing articles Show Details

T=20°C; Hydrolysis; 0.0833333 h;

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Rx-ID: 5322686 Find similar reactions

92%

With copper diacetate; ethylene glycol

T=50°C; P=760.051 Torr; 12 h; Green chemistry; Reagent/catalystTemperatureSolvent; chemoselective reaction;

Jiang, Jian-An; Chen, Cheng; Huang, Jian-Gang; Liu, Hong-Wei; Cao, Song; Ji, Ya-Fei

Green Chemistry, 2014 , vol. 16, # 3 p. 1248 - 1254 Title/Abstract Full Text View citing articles Show Details

91%

With oxygen; diethylamine; copper(l) chloride in methanol

T=20°C;

Tripathi; Sama; Taneja

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010 , vol. 49, # 3 p. 379 - 381 Title/Abstract Full Text View citing articles Show Details

91%

With oxygen; cobalt(II) diacetate tetrahydrate; sodium hydroxide in ethylene glycol

T=80°C; P=760.051 Torr; 4 h; Hide Experimental Procedure

Jiang, Jian-An; Du, Jia-Lei; Liao, Dao-Hua; Wang, Zhan-Guo; Ji, Ya-Fei

Tetrahedron Letters, 2014 , vol. 55, # 8 p. 1406 - 1411 Title/Abstract Full Text View citing articles Show Details

General procedure

General procedure: a mixture of substrate 1a(1 mmol), cobalt salt (n1molpercent) and NaOH (n2 equiv)in EG (5 mL) was stirred with O2 (1 atm) being bubbled, under 80 oCfor 8 h. Hydrochloric acid (10 mL, 2percent) and methyl tert-butyl ether (MTBE, 10 mL) were successively added to the reactionmixture. The organic layer was separated, and the aqueous phase was furtherextracted with MTBE(10 mL × 2). The combined organic phase was dried over anhydrous sodium sulfateand concentrated to give a residue, which was purified by column chromatographyon silica gel (eluents: petroleum ether/ethyl acetate, 10/1) to provide thedesired products 2a.

91%

With oxygen; cobalt(II) acetate; sodium hydroxide in water; ethylene glycol

T=50°C; P=760.051 Torr; 12 h; Green chemistry; chemoselective reaction; Hide Experimental Procedure

Jiang, Jian-An; Du, Jia-Lei; Zhang, Zhong-Nan; Zhai, Jiao-Jiao; Ji, Ya-Fei

Synthetic Communications, 2014 , vol. 44, # 10 p. 1430 - 1440 Title/Abstract Full Text View citing articles Show Details

2.2. Typical procedure for the Co(OAc)2-catalyzed aerobic oxidation of 1 (Table 2 in the text)

General procedure: Typical procedure: a mixture of substrate 1 (5.0 mmol), Co(OAc)2*4H2O (0.05 mmol, 12 mg) and NaOH (5.0 mmol, 0.2 g) in EG/H2O (5.0 mL/0.25 mL) was stirred with O2 (1.0 atm) being bubbled at 50 °C for 12 h. Hydrochloric acid (10.0 mL, 2 percent) and chloroform (10.0 mL) were successively added to the reaction mixture. The chloroform phase was separated, and the aqueous phase was further extracted with chloroform (10.0 mL × 2). The combined organic layer was dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography on silica gel (eluents: .petroleum ether/ethyl acetate, 5/1) to provide the desired products 2. 95 % Chromat.

With N-Bromosuccinimide in dimethyl sulfoxide

T=120°C; Oxidation; 1 h;

Baik, Woonphil; Lee, Hyun Joo; Jang, Jung Min; Koo, Sangho; Kim, Byeong Hyo

Journal of Organic Chemistry, 2000 , vol. 65, # 1 p. 108 - 115 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: copper diacetate / 12 h / 50 °C / 760.05 Torr / |Inert atmosphere; |Green chemistry 2: ethylene glycol; copper diacetate / 8 h / 50 °C / |Green chemistry View Scheme

Jiang, Jian-An; Chen, Cheng; Huang, Jian-Gang; Liu, Hong-Wei; Cao, Song; Ji, Ya-Fei

Green Chemistry, 2014 , vol. 16, # 3 p. 1248 - 1254 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: copper diacetate / 4 h / 50 °C / |Green chemistry 2: ethylene glycol; copper diacetate / 8 h / 50 °C / |Green chemistry View Scheme

Jiang, Jian-An; Chen, Cheng; Huang, Jian-Gang; Liu, Hong-Wei; Cao, Song; Ji, Ya-Fei

Green Chemistry, 2014 , vol. 16, # 3 p. 1248 - 1254 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5701711 Find similar reactions

T=40°C;

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Sharp

Journal of the Chemical Society, 1937 , p. 852 Full Text Show Details

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Rx-ID: 6083842 Find similar reactions

Herstellung von 4-Hydroxy-3,5-dimethoxy-<α-14C>benzaldehyd;

Kratzl; Billek

Monatshefte fuer Chemie, 1954 , vol. 85, p. 845,854 Full Text View citing articles Show Details

Ciaramitaro,D.; Steelink,C.

Phytochemistry (Elsevier), 1975 , vol. 14, p. 543 - 552 Full Text View citing articles Show Details

Hansson; Wickberg

Synthesis, 1976 , p. 191 Full Text Show Details

Gulf Oil Corp., Pittsburgh, Pa (V. St. A.)

Patent: DE2617585 , 1976 ; Chem.Abstr., vol. 86, # 55159 Full Text Show Details

Bu'lock; Walker

Journal of the Chemical Society [Section] C: Organic, 1967 , p. 336 Full Text Show Details

Hide Experimental Procedure

Hoffmann-La Roche Inc.

Patent: US4218567 A1, 1980 ; Title/Abstract Full Text Show Details

2:Preparation of 3,5-dimethoxy-4-hydroxybenzaldehyde

EXAMPLE 2 Preparation of 3,5-dimethoxy-4-hydroxybenzaldehyde Into a 2-l., 3-necked, round-bottomed flask equipped with a mechanical stirrer, thermometer, and a condenser was added 700 ml. of methanol. 68.0 G. of clean sodium was then added in small pieces and under nitrogen. After the reaction was complete, the methanol was removed in vacuo at 45°-50° and to the residue was added 312 ml. of dimethylformamide and 156 ml. of methanol. 5.85 G. of cuprous chloride was added followed, after 5 minutes, by 165 g. of 3,5-dibromo-4-hydroxybenzaldehyde, an exotherm resulted (25° to 50° during 5 minutes). The mixture was heated under reflux for 4 hours, the solvents were evaporated in vacuo (0.1 torr) at 55°, and the residue was treated with 440 ml. of 15percent brine. The mixture was stirred at room temperature for 30 minutes, again cooled to 0°, and filtered over 100 g. of celite. The filter cake was washed with three 250 ml. portions, a total of 750 ml. of cold (5°) water (that is, until neutral) followed, after discarding the aqueous washings, by three 500 ml. portions, a total of 1.5 l. of hot (60°) ethyl acetate. The ethyl acetate washings were added to a separatory funnel, excess water (about 10 ml.) was removed, and the ethyl acetate dried over magnesium sulfate and evaporated to give 95.0 g. (88.5percent) of 3,5-dimethoxy-4-hydroxybenzaldehyde as a yellow solid, mp 107°-109°. GLC indicated a purity of 99.7percent.

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Hoffmann-La Roche Inc.

Patent: US4218567 A1, 1980 ; Title/Abstract Full Text Show Details

4:Preparation of 3,5-dimethoxy-4-hydroxybenzaldehyde

EXAMPLE 4 Preparation of 3,5-dimethoxy-4-hydroxybenzaldehyde Into a 5-l., 3-necked, round-bottomed flask equipped with a mechanical stirrer, thermometer, and condenser was added 1.0 l. of methanol. 85.2 G. of clean sodium was then added in small pieces and under nitrogen. After the reaction was complete, the methanol was removed at 45°-50° and 450 ml. of dimethylformamide added to the residue. To the rapidly stirred slurry of sodium methoxide in dimethylformamide was added 10.7 g. of cuprous chloride to give a deep blue mixture which was stirred at 25° for 15 minutes. 214.4 G. of 3-methoxy-4-hydroxy-5-bromobenzaldehyde was added during 3 minutes, whereupon a slight exotherm ensued. The temperature of the reaction was increased to 97° during 15 minutes and the mixture was stirred at this temperature for 1.75 hours. The reaction was cooled to 60° and the dimethylformamide distilled off under high vacuum. 1.0 l. of 15percent brine was added to the residue, the mixture was stirred at 50° for 30 minutes, cooled to 0° and treated with 300 ml. of cold (0°) concentrated hydrochloric acid at such a rate that the temperature was kept below 15°. The mixture was stirred at room temperature for 1 hour, again cooled to 0° and filtered over 100 g. of celite. The filter cake was washed with four 400 ml. portions, a total of 1.6 l. of cold (5°) water, followed, after discarding the aqueous wash, by five 500 ml. portions, a total of 2.5 l. of hot (60°) ethyl acetate. The ethyl acetate washings were added to a separatory funnel, excess water (about 15 ml.) was ran off, and the ethyl acetate dried over magnesium sulfate and evaporated in vacuo to give 154.0 g. (91percent) of 3,5-dimethoxy-4-hydroxybenzaldehyde as yellow crystals, mp 109°-111°, purity of 99.72percent.

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Hoffmann-La Roche Inc.

Patent: US4218567 A1, 1980 ; Title/Abstract Full Text Show Details

8:Preparation of 3,5-dimethoxy-4-hydroxybenzaldehyde

EXAMPLE 8 Preparation of 3,5-dimethoxy-4-hydroxybenzaldehyde A 5-l., 3-necked, round-bottomed flask equipped with a mechanical stirrer, condenser capped with a drying tube, and a thermometer was charged with 1.2 l. of methanol. 109.5 G. of clean sodium was then added in small pieces and under nitrogen. When all the sodium had reacted, the methanol was removed in vacuo at 50° and a mixture of 500 ml. of dimethylformamide and 250 ml. of methanol added to the residue. To the vigorously stirred solution was added 9.45 g. of cuprous chloride followed, after 5 minutes, by 264.4 g. of 3,5-dibromo-4-hydroxybenzaldehyde. An exotherm resulted in which the temperature rose from 23° to 50° over a period of 10 minutes. The mixture was stirred at 95° for 3.25 hours, during which time the color of the reaction changed from blue to greyish-green.

The solvents were removed in vacuo at 45° and to the residue was added 700 ml. of 15percent brine. The mixture was stirred at 60° for 30 minutes, cooled to 0° and treated with 400 ml. of cold (0°) concentrated hydrochloric acid at such a rate that the temperature was kept below 30°. The mixture was stirred at room temperature for 30 minutes, then at 0° for another 30 minutes, and filtered over 100 g. of celite. The filter cake was washed with four 400 ml. portions, a total of 1.6 l. of cold (5°) water, followed, after removing the aqueous washings, by four 500 ml. portions, a total of 2.0 l. of hot (60°) ethyl acetate. The ethyl acetate washings were added to a separatory funnel, excess water (about 20 ml.) was removed, and the ethyl acetate dried over magnesium sulfate and evaporated to give 153.3 g. (88percent) of 3,5-dimethoxy-4-hydroxybenzaldehyde as a pale yellow solid, mp 105°-108°. Purity of 99.38percent.

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Rx-ID: 6083843 Find similar reactions

With sodium hydroxide

Spaeth

Monatshefte fuer Chemie, 1920 , vol. 41, p. 278 Full Text Show Details

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Rx-ID: 6083844 Find similar reactions

With emulsin

Koerner

Gazzetta Chimica Italiana, 1888 , vol. 18, p. 215 Full Text Show Details

With sulfuric acid

Koerner

Gazzetta Chimica Italiana, 1888 , vol. 18, p. 215 Full Text Show Details

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Rx-ID: 6083845 Find similar reactions

With sodium hydrogensulfite

anschliessend Erwaermen mit wss.NaOH;

Leger; Hibbert

Journal of the American Chemical Society, 1938 , Full Text View citing articles Show Details

Hibbert; Steeves

Journal of the American Chemical Society, 1937 , Full Text View citing articles Show Details

Bell et al.

Journal of the American Chemical Society, 1937 , Full Text View citing articles Show Details

Hawkins; Wright; Hibbert

Journal of the American Chemical Society, 1937 , Full Text View citing articles Show Details

vol. 60, p. 565 vol. 59, p. 1768 vol. 59, p. 598 vol. 59, p. 2447

With sodium hydroxide; nitrobenzene

T=160°C;

Creighton; Hibbert

Journal of the American Chemical Society, 1944 , vol. 66, p. 37 Full Text View citing articles Show Details

Creighton; Gibbs; Hibbert

Journal of the American Chemical Society, 1944 , vol. 66, p. 32,35 Full Text Show Details

Creighton; McCarthy; Hibbert

Journal of the American Chemical Society, 1941 , vol. 63, p. 312,3049,3050 Full Text View citing articles Show Details

With hydrogenchloride

Kulka; Hibbert

Journal of the American Chemical Society, 1943 , Full Text View citing articles Show Details

Pyle; Brickman; Hibbert

Journal of the American Chemical Society, 1939 , Full Text View citing articles Show Details

MacInnes et al.

Journal of the American Chemical Society, 1940 , Full Text Show Details

West et al.

Journal of the American Chemical Society, 1939 , Full Text View citing articles Show Details

vol. 65, p. 1185 vol. 61, p. 2198 vol. 62, p. 2803,2805 vol. 61, p. 2556

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in gepufferter wss. Loesung (pH 8);

Richtzenhain

Chemische Berichte, 1944 , vol. 77/79, p. 409,416 Full Text View citing articles Show Details

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Rx-ID: 7448653 Find similar reactions

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Pearl

Journal of the American Chemical Society, 1948 , vol. 70, p. 1746 Full Text View citing articles Show Details

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B: 61.5%

With sodium hydroxide; nitrobenzene; PEG-400; 1,10phenanthroline in water

T=170°C; Oxidation; 3 h;

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Gogotov; Rybal'chenko; Makovskaya; Babkin

Russian Chemical Bulletin, 1996 , vol. 45, # 12 p. 2854 - 2857 Title/Abstract Full Text View citing articles Show Details

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B: 52.2%

With sodium hydroxide; nitrobenzene; 1,10-phenanthroline in water

T=170°C; Oxidation; 3 h;

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Gogotov; Rybal'chenko; Makovskaya; Babkin

Russian Chemical Bulletin, 1996 , vol. 45, # 12 p. 2854 - 2857 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9261486

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With N,N,N-triethylamine N-oxide in methanol

3 h;

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Zubaidha; Bhosale; Hashmi

Tetrahedron Letters, 2002 , vol. 43, # 40 p. 7277 - 7279 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 11645842 Find similar reactions

Zabinski, Jerzy; Wolska, Irena; Maciejewska, Dorota

Journal of Molecular Structure, 2007 , vol. 833, # 1-3 p. 74 - 81 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12099118 Find similar reactions

Zou, Hong Bin; Dong, Sheng Yi; Zhou, Chang Xin; Hu, Li Hong; Wu, Yi Hang; Li, Hai Bo; Gong, Jing Xu; Sun, Lian Li; Wu, Xiu Mei; Bai, Hua; Fan, Bo Tao; Hao, Xiao Jiang; Stoeckigt, Joachim; Zhao, Yu

Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 6 p. 2060 - 2071 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12099682 Find similar reactions

Zou, Hong Bin; Dong, Sheng Yi; Zhou, Chang Xin; Hu, Li Hong; Wu, Yi Hang; Li, Hai Bo; Gong, Jing Xu; Sun, Lian Li; Wu, Xiu Mei; Bai, Hua; Fan, Bo Tao; Hao, Xiao Jiang; Stoeckigt, Joachim; Zhao, Yu

Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 6 p. 2060 - 2071

Title/Abstract Full Text View citing articles Show Details

2: 85 percent / pyridinium chlorochromate / CH2Cl2 / 20 °C 3: 92 percent / NaH; PhSH; HMPT / toluene / Heating View Scheme

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Multi-step reaction with 2 steps 1: 60 percent / NaOH, Cu / H2O / 25.5 h / 101 °C 2: Na2CO3 / acetone / 5 h / Heating View Scheme

Rx-ID: 16913830 Find similar reactions

Ellis, James E.; Lenger, Steven R.

Synthetic Communications, 1998 , vol. 28, # 9 p. 1517 - 1524 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 48.5 g / Br2, AcOH 2: 18 g / CuCl2 / dimethylformamide / 1 h / 120 °C View Scheme

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Puri, S. C.; Anand, S. M.; Atal, C. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985 , vol. 24, p. 294 - 295 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 95 percent / Br2 / acetic acid / 1 h 2: 83 percent / CuCl2 / dimethylformamide; methanol / 1 h / 100

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Rao, Durvasula V.; Stuber, F. A.

Synthesis, 1983 , # 4 p. 308 Title/Abstract Full Text Show Details

°C View Scheme

Multi-step reaction with 2 steps 1: 95 percent / Br2 / methanol / 1 h / Ambient temperature 2: 91 percent / Cu2Cl2 / dimethylformamide / 2.5 h / 97 °C View Scheme

Manchand, Percy S.; Belica, Peter S.; Wong, Harry S.

Synthetic Communications, 1990 , vol. 20, # 17 p. 2659 - 2666 Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: bromine / methanol 2: copper(l) chloride / N,N-dimethyl-formamide View Scheme

Li, Yan; Dai, Fang; Jin, Xiao-Ling; Ma, Meng-Meng; Wang, Yi-Hua; Ren, Xiao-Rong; Zhou, Bo

Food Chemistry, 2014 , vol. 158, p. 41 - 47 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 21713992 Find similar reactions

Manchand, Percy S.; Belica, Peter S.; Wong, Harry S.

Synthetic Communications, 1990 , vol. 20, # 17 p. 2659 - 2666 Title/Abstract Full Text Show Details

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Rx-ID: 21721941 Find similar reactions

Manchand, Percy S.; Belica, Peter S.; Wong, Harry S.

Synthetic Communications, 1990 , vol. 20, # 17 p. 2659 - 2666 Title/Abstract Full Text Show Details

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Rx-ID: 21749848 Find similar reactions

Manchand, Percy S.; Belica, Peter S.; Wong, Harry S.

Synthetic Communications, 1990 , vol. 20, # 17 p. 2659 - 2666 Title/Abstract Full Text Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: durch aufeinanderfolgende Verseifung und Oxydation mit Kupfersulfat 2: dimethyl-p-toluidine View Scheme

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Rx-ID: 22058168 Find similar reactions

Mauthner

Justus Liebigs Annalen der Chemie, 1913 , vol. 395, p. 279 Full Text Show Details

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Rx-ID: 22080862 Find similar reactions

Pearl

Journal of the American Chemical Society, 1948 , vol. 70, p. 1746 Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: toluene; palladium/barium sulfate / 110 °C / Hydrogenation 2: ethanol; aq. NaOH solution; hydrogen View Scheme

Rx-ID: 22103221 Find similar reactions

Mauthner

Journal fuer Praktische Chemie (Leipzig), 1935 , vol. <2> 142, p. 26,31 Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: pyridine; SOCl2

2: palladium/BaSO4; xylene / Hydrogenation 3: CHCl3; methanol. sodium methylate View Scheme

Rx-ID: 22395418 Find similar reactions

Freudenberg; Huebner

Chemische Berichte, 1952 , vol. 85, p. 1181,1188 Full Text View citing articles Show Details

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A: 92%

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Rx-ID: 25859063 Find similar reactions

EMD CHEMICALS, INC.

Patent: US2004/247536 A1, 2004 ; Title/Abstract Full Text Show Details

I:2-Ethylhexyl-alpha-aceto-3,5-dimethoxy-4-hydroxy cinnamate

Example I

2-Ethylhexyl-alpha-aceto-3,5-dimethoxy-4-hydroxy cinnamate Monodemethylation of 3,4,5-trimethoxy benzaldehyde using sulphuric acid at 40° C. for 8 hours yields 3,5-Dimethoxy-4-hydroxy benzaldehyde (Syringaldehyde). Condensation of syringaldehyde with 2-ethylhexyl acetoacetate in the presence of piperidine-acetic acid and benzene as the reaction medium at reflux temperature under continuous azeotropic water removal yields the title product. The reaction takes about 1.5 hours for completion. The yield obtained is typically 92percent. A

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A: 2.49 %Chromat. B: 4.56 %Chromat. C: 11.51 %Chromat.

With water; oxygen; sodium hydroxide

T=120°C; P=15001.5 Torr;

Zhang, Junhua; Deng, Haibo; Lin, Lu

Molecules, 2009 , vol. 14, # 8 p. 2747 - 2757 Title/Abstract Full Text View citing articles Show Details

With nitrobenzene

AutoclaveAlkaline conditions;

Yang, Xiao-Hui; Zhang, Ping-Hu; Zhou, Yong-Hong; Liu, Cheng-Guo; Lin, Xiao-Yu; Cui, Jing-Fang

Arkivoc, 2011 , vol. 2011, # 10 p. 327 - 337 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 31162057 Find similar reactions

With sorgum caffeic acid O-methyltransferase (Bmr12); sulfolobus S-adenosylhomocysteine hydrolase in water; N,N-dimethyl-formamide

T=37°C; pH=7.5; aq. bufferEnzymatic reaction; Kinetics;

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Palmer, Nathan A.; Sattler, Scott E.; Saathoff, Aaron J.; Sarath, Gautam

Journal of Agricultural and Food Chemistry, 2010 , vol. 58, # 9 p. 5220 - 5226 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 32612034 Find similar reactions

A: 73%

With sodium carbonate in acetone

6 h; Reflux; Hide Experimental Procedure

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Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.-Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung

European Journal of Medicinal Chemistry, 2012 , vol. 48, p. 371 - 378 Title/Abstract Full Text View citing articles Show Details

5.2.7. 3-Hydroxy-4,5-dimethoxybenzaldehyde (15)

A mixture of 14 (25 g, 148.8 mmol), (CH3)2SO4 (18.75 g, 148.8 mmol), and Na2CO3 (17.5 g, 165.1 mmol) was slurred into acetone and further reflux for 6 h. The resulting crude was further purified by column chromatography to obtain an oil and this was readily crystallized to give 15 (19.8 g, 73percent), m.p. 65-67 °C; IR (neat) νmax 3414, 2943, 2843, 1689, 1589, 1504, 1462, 1338, 1203, 1134, 995, 837, 752, 702 cm-1; 1HNMR (300 MHz, DMSO-d6) δ 9.78 (1H, s, CHO), 9.71 (1H, s, OH), 7.03 (2H, s), 3.83 (3H, s, OMe), 3.76 (3H, s, OMe); 13CNMR (75 MHz, DMSO-d6) δ 191.8, 153.5, 151.0, 141.8, 131.6, 111.0, 104.3, 59.9, 55.8; EIMS m/z (rel. int.): 182 [M]+ (100), 167 (35), 111 (26), 93 (11); HREIMS calcd for C9H10O4 [M]+ 182.0579, found 182.0576. A

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Multi-step reaction with 2 steps 1.1: copper; sodium hydroxide / water / Reflux 1.2: Reflux 2.1: sodium carbonate / acetone / 6 h / Reflux View Scheme

Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.-Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung

European Journal of Medicinal Chemistry, 2012 , vol. 48, p. 371 - 378 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1.1: bromine; acetic acid / 1.5 h 2.1: copper; sodium hydroxide / water / Reflux 2.2: Reflux 3.1: sodium carbonate / acetone / 6 h / Reflux View Scheme

Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.-Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung

European Journal of Medicinal Chemistry, 2012 , vol. 48, p. 371 - 378 Title/Abstract Full Text View citing articles Show Details

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KineticsMechanism; pHvalueConcentrationTemperatureReagent/catalyst;

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Rx-ID: 34529951 Find similar reactions

Kulkarni; Bongane; Gavali; Patel

Journal of the Indian Chemical Society, 2012 , vol. 89, # 10 p. 1347 - 1350 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 35259189 Find similar reactions

A: 6.2% B: 14.7% C: 8.8%

With oxygen; copper(II) sulfate; isobutyl methylketone

T=175°C; P=18751.9 Torr; 1.5 h; Ionic liquid; ConcentrationTimeTemperatureSolvent;

Liu, Shiwei; Shi, Zhongliang; Li, Lu; Yu, Shitao; Xie, Congxia; Song, Zhanqian

RSC Advances, 2013 , vol. 3, # 17 p. 5789 - 5793 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 35259190 Find similar reactions

A: 10.5% B: 5.4%

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Liu, Shiwei; Shi, Zhongliang; Li, Lu; Yu, Shitao; Xie, Congxia; Song, Zhanqian

RSC Advances, 2013 , vol. 3, # 17 p. 5789 - 5793 Title/Abstract Full Text View citing articles Show Details

With oxygen; copper(II) sulfate

T=175°C; P=22502.3 Torr; 1.5 h; Ionic liquid;

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Synthesize Find similar Rx-ID: 37061181 Find similar reactions

A: 9 %Spectr. B: 82 %Spectr. C: 25 %Spectr. D: 6 %Spectr.

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; (CuOTf)2*C6H5CH3; oxygen in toluene

T=100°C; 36.0833 h; Schlenk techniqueSealed tube; chemoselective reaction;

Sedai, Baburam; Diaz-Urrutia, Christian; Baker, R. Tom; Wu, Ruilian; Silks, L. A. Pete; Hanson, Susan K.

ACS Catalysis, 2013 , vol. 3, # 12 p. 3111 - 3122 Title/Abstract Full Text View citing articles Show Details

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With copper diacetate; ethylene glycol

T=50°C; 8 h; Green chemistry; chemoselective reaction;

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Rx-ID: 37471112 Find similar reactions

Jiang, Jian-An; Chen, Cheng; Huang, Jian-Gang; Liu, Hong-Wei; Cao, Song; Ji, Ya-Fei

Green Chemistry, 2014 , vol. 16, # 3 p. 1248 - 1254 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 37471113 Find similar reactions

94%

With copper diacetate; ethylene glycol

T=50°C; 8 h; Green chemistry; chemoselective reaction;

Jiang, Jian-An; Chen, Cheng; Huang, Jian-Gang; Liu, Hong-Wei; Cao, Song; Ji, Ya-Fei

Green Chemistry, 2014 , vol. 16, # 3 p. 1248 - 1254 Title/Abstract Full Text View citing articles Show Details

92%

With oxygen; cobalt(II) acetate; sodium hydroxide in water; ethylene glycol

T=50°C; P=760.051 Torr; 12 h; Green chemistry;

Jiang, Jian-An; Du, Jia-Lei; Zhang, Zhong-Nan; Zhai, Jiao-Jiao; Ji, Ya-Fei

Synthetic Communications, 2014 , vol. 44, # 10 p. 1430 - 1440 Title/Abstract Full Text View citing articles Show Details

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T=50°C; pH=2;

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Rx-ID: 39163500 Find similar reactions

Popova; Beloglazova; Bogolitsyn; Tortseva; Verkholomova; Pokryshkin

Russian Journal of General Chemistry, 2014 , vol. 84, # 11 p. 2092 - 2097 Zh. Obshch. Khim., 2014 , vol. 84, # 11 p. 1794 - 1799,6 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 39373755 Find similar reactions

With anhydrous iron chloride in water

T=130°C; 2 h; Ionic liquid;

Yi, Fengping; Jiang, Xiaoyan; Niu, Jihua; Zhang, Lirong; Wang, Zhen

Asian Journal of Chemistry, 2015 , vol. 27, # 3 p. 885 - 888 Title/Abstract Full Text View citing articles Show Details

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With sodium persulfate; Ir(2-(2,4-difluorophenyl)-5(trifluoromethyl)pyridine)2(4,4’-di-tert-butyl-2,2’bipyridine)PF6; palladium diacetate in N,N-dimethyl-formamide

T=20°C; 15 h; Irradiation; chemoselective reaction;

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Rx-ID: 44160112 Find similar reactions

Kärkäs, Markus D.; Bosque, Irene; Matsuura, Bryan S.; Stephenson, Corey R. J.

Organic Letters, 2016 , vol. 18, # 19 p. 5166 - 5169 Title/Abstract Full Text View citing articles Show Details

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With toluene-4-sulfonic acid in neat (no solvent, solid phase) T=20°C; 0.583333 h; Green chemistry; Hide Experimental Procedure

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Rx-ID: 45724436 Find similar reactions

Pandurangan, Nanjan

Letters in Organic Chemistry, 2017 , vol. 14, # 4 p. 231 - 235 Title/Abstract Full Text Show Details

MOM Deprotection by pTSA

General procedure: MOM ether (5 mmol) and pTSA.H2O (7.7 mmol) weretriturated well in a mortar for 5 min (in the case of entry 10trituration time was about 15 min), reaction mixture was leftat room temperature for another 30 min. After completion ofthe reaction (monitored by TLC), cold water (4oC) wasadded. The products were separated by centrifugation. Theyields of the products ranged from 85-98percent. The purities andthe identities of the products were established by direct comparisonwith known compounds (TLC, Mp and IR). See supplementaryinformation for further details.

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T=90°C; 24 h;

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Rx-ID: 9030246 Find similar reactions

Tuck, Kellie L.; Hayball, Peter J.

Journal of Labelled Compounds and Radiopharmaceuticals, 2001 , vol. 44, # 14 p. 1005 - 1012 Title/Abstract Full Text Show Details

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Rx-ID: 7406770 Find similar reactions

Amid d. unmark. O-Benzyl-syringasaeure (mehrere Stufen);

Freudenberg; Reichert

Naturwissenschaften, 1954 , vol. 41, p. 229 Full Text View citing articles Show Details

4-Brom-2,6-dimethoxy-phenol, 1. Cu14CN, 2. Raney-Nickel, NaH2PO2, Reduktion;

Billek et al.

Journal of Labelled Compounds, 1969 , vol. 5, p. 3,7 Full Text Show Details

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Rx-ID: 10399428 Find similar reactions

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With 5-O-methyltransferase; caffeic acid; 3-(4,5-dihydroxy-3methoxyphenyl)prop-2-enoic acid

Enzyme kinetics; Further Variations:Reagents;

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Kota, Parvathi; Guo, Dianjing; Zubieta, Chloe; Noel, Joe; Dixon, Richard A.

Phytochemistry, 2004 , vol. 65, # 7 p. 837 - 846 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 11261464 Find similar reactions

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Stage #1: 3-[2H3]methoxy-4-hydroxybenzaldehyde With sodium hydroxide; iodine; potassium iodide in water

T=20°C; 8 h;

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Sakakibara, Norikazu; Nakatsubo, Tomoyuki; Suzuki, Shiro; Shibata, Daisuke; Shimada, Mikio; Umezawa, Toshiaki

Organic and Biomolecular Chemistry, 2007 , vol. 5, # 5 p. 802 - 815 Title/Abstract Full Text View citing articles Show Details

Stage #2: sodium methylate With copper

T=128°C; 3 h; Further stages.;

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Rx-ID: 9189517 Find similar reactions

40.5%

With sulfuric acid; boric acid in glycerol

T=110°C; 1 h;

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Yamauchi, Kazuchika; Yasuda, Seiichi; Fukushima, Kazuhiko

Journal of agricultural and food chemistry, 2002 , vol. 50, # 11 p. 3222 - 3227 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9388028 Find similar reactions

With sodium

T=128°C; 3 h;

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Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio

Organic and biomolecular chemistry, 2003 , vol. 1, # 14 p. 2474 - 2485 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: I2; KI; aq. NaOH / 2 h / 20 °C 2: Na / 3 h / 128 °C View Scheme

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Rx-ID: 14046247 Find similar reactions

Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio

Organic and biomolecular chemistry, 2003 , vol. 1, # 14 p. 2474 - 2485 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: aq. HCl / acetic acid / 1 h / Heating 2: I2; KI; aq. NaOH / 2 h / 20 °C 3: Na / 3 h / 128 °C View Scheme

Rx-ID: 14054186 Find similar reactions

Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio

Organic and biomolecular chemistry, 2003 , vol. 1, # 14 p. 2474 - 2485 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 67 percent / CuCl2 / dimethylformamide; tetradeuteriomethanol / 1 h / Heating 2: 40.5 percent / boric acid; aq. H2SO4 / glycerol / 1 h / 110 °C View Scheme

Rx-ID: 14472923 Find similar reactions

Yamauchi, Kazuchika; Yasuda, Seiichi; Fukushima, Kazuhiko

Journal of agricultural and food chemistry, 2002 , vol. 50, # 11 p. 3222 - 3227 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 8603883 Find similar reactions

With air

Oxidation; Formation of xenobiotics; Further byproducts given;

Kjaellstrand, Jennica; Ramnaes, Olle; Petersson, Goeran

Chemosphere, 2000 , vol. 41, # 5 p. 735 - 741 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 4892260 Find similar reactions

A: 70% B: 10%

With sodium carbonate in acetone

5 h; Heating;

Ellis, James E.; Lenger, Steven R.

Synthetic Communications, 1998 , vol. 28, # 9 p. 1517 - 1524 Title/Abstract Full Text View citing articles Show Details

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With oxygen; copper(II) sulfate; sodium hydroxide in water

T=170°C; P=6375.64 Torr; Autoclave; Catalytic behavior; Reagent/catalyst; Overall yield = 9.5 percent;

Alunga, Kissa R.; Ye, Yue-Yuan; Li, Shui-Rong; Wang, Duo; Liu, Yun-Quan

Catalysis Science and Technology, 2015 , vol. 5, # 7 p. 3746 - 3753 Title/Abstract Full Text View citing articles Show Details

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A: 26%

With Stichococcus bacillaris 155LTAP

DellaGreca, Marina; Pinto, Gabriele; Pollio, Antonino; Previtera, Lucio; Temussi, Fabio

B: 13% C: 8%

Microbiological reaction;

Tetrahedron Letters, 2003 , vol. 44, # 14 p. 2779 - 2780 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 29377398 Find similar reactions

With oxygen; 12-molybdophosphoric acid HPMo in water

T=170°C; P=3825.38 Torr; Hide Experimental Procedure

ETH ZURICH

Patent: US2010/121110 A1, 2010 ; Location in patent: Page/Page column 5-8 ; Title/Abstract Full Text Show Details

11:

Experiments 01-11 and Blank Sample (see Table 1):In a typical experiment, 9.13 g of the POM H3PMo12O40 were dissolved in 100 ml of water or a water/alcohol mixture, which corresponds formally to a 0.05 molar solution. This was then transferred into a 500 ml autoclave (Premex Reactor AG, Lengnau, Switzerland). Before the closure of the reactor, 1 g of pulverulent lignin was added. The reaction mixture was then contacted three times with 5 bar of oxygen or nitrogen and vented, in order to displace the air initially present. Finally, the reactor was filled with 5 bar of oxygen or 10 bar of nitrogen. The reaction mixture was heated to 170° C. at a rate of 8 K/min at a stirrer speed of 1200 rad/min. The mixture was kept at 170° C. for 20 minutes. The liquid phase was removed after 20 minutes. This was followed by the sampling through a water-cooled cooling coil. The sample was filtered once and then extracted three times with 10 ml of chloroform. 30 μl of n-decane were added to the organic phase as an internal standard for the GC-MS analysis (Fisons instruments GC8000/MD800; column from Restek Rtx-5MS 30 m.x.0.25 mm.x.0.25 μm).In experiments 03, 04, 08, 09, 10 and 11, free-radical scavengers (methanol, ethanol) were used.In experiment 02, a second liquid phase in the form of 30 ml of chloroform was added before the closure of the reactor.In experiment 05, 9.45 g of the POM Na3PMo12O40 were used. In the blank sample, no POM was used.Experiment 12 and Wu et al. (G. X. Wu, M. Heitz, E. Chornet, Ind. Eng. Chem. Res. 33, 718 (March, 1994)) (see table 1):The experimental method in experiment 12 is kept analogous to Wu et al. 10 g of lignin were dissolved in 100 ml of a 3 molar sodium hydroxide solution. The solution was added to a 500 ml autoclave, and the catalyst system consisting of 500 mg of copper sulfate and 50 mg of iron chloride was added. The reactor was closed and filled three times with oxygen at 10 bar and emptied, in order to displace the air originally present. Subsequently, the reaction vessel was placed under pressure with 13.2 bar of oxygen. The reaction mixture was heated to 170° C. at a rate of 8 K/min at a stirrer speed of 1200 rad/min. The mixture was kept at 170° C. for 20 minutes. The liquid phase was withdrawn after 20 minutes. The sampling was effected through a water-cooled cooling coil.In experiment 01, lignin was treated in a 0.05 molar aqueous H3PMo12O40 solution under inert gas. In the course of this, the color of the solution changed from yellowish to dark blue. This shows clearly that the polymolybdate used was reduced. By means of GC-MS analysis, 0.56 mg of lignin-based products (principally vanillin) was quantified.The yield of lignin-based products could be increased by approx. 30percent by in situ extraction (cf. experiment 01 with experiment O2). To this end, a second liquid phase (chloroform) was added to the reaction mixture. This has a higher solubility for the desired degradation products and can therefore withdraw any products formed from the actual reaction medium (aqueous POM solution) before possible further reactions destroy the products formed again.The degradation of lignin with 0.05 molar H3PMo12O40 solution under oxygen (experiment 06) likewise increased the yield compared to the degradation under inert gas (experiment 01). After the experiment under oxygen, in contrast to the experiment under inert gas, only slight discoloration of the solution to yellow-greenish was detected, i.e. the polyoxomolybdate was reduced only very slightly, if at all. This leads to the suspicion that the POM is reoxidizable under the conditions used and, in this case, oxygen is consumed by the POM during the degradation of lignin.Experiment 07 shows that various lignin types can be used and that the yield of chemicals here is within the same order of magnitude. According to the manufacturer, the lignin from Aldrich (batch No. 09724CE) is a softwood lignin (principally from spruce wood), which was obtained in the Kraft process. The lignin from the Granit.(R). process was, in contrast, obtained from plants utilized in agriculture and therefore has a different chemical structure.In experiment 05, the POM used was the sodium salt Na3PMo12O40 corresponding to H3PMo12O40. The yield of chemicals is noticeably higher in this experiment. It is therefore found that changes in the POM system used which are slight from a chemical point of view can affect the yield of desired products. The use of a very substantially optimal POM system is therefore of crucial significance for the attainment of high yields.The positive effect of the free-radical scavenger with regard to the yield of chemicals was demonstrated in experiments 03 and 04 compared to experiment 01 and the blank sample. In experiments 03 and 04, ethanol and methanol were used as free-radical scavengers. Using the freeradical scavengers, the yield was enhanced from 0.56 mg to 1.17 mg in the case of ethanol and to 2.38 mg in the case of methanol.In the case of the blank sample without POM, no lignin-based products were detectable.FIG. 1 shows the corresponding GC-MS chromatograms and illustrates that not only are the amounts of vanillin and 4-hydroxyacetyl-2-methoxyphenol produced greater when the free-radical scavengers are used, but novel components are also prepared in amounts comparable to vanillin.The formation of vanillic acid methyl ester in experiment 04 shows that methanol is incorporated into the product (see equation 11).Using ethanol as the free-radical scavenger, in contrast, vanillic acid ethyl ester is formed (see equation 12).In addition, experiments were carried out to verify the mechanism indicated in equations 11 and 12. With deuterated methanol CD3OD, it was possible to show clearly that a methanol radical is incorporated into the vanillic acid methyl ester product. The molecular weight of vanillic acid methyl ester produced in reactions of lignin in the presence of undeuterated methanol was determined by means of GC-MS analysis to be 182 g/mol. Using deuterated methanol, the molecular weight was determined to be 185 g/mol. In addition, it was checked whether the formation of the vanillic acid methyl ester is also possible from vanillin, for example via the reaction route of vanillin vanillic acid vanillic acid methyl ester. The treatment of vanillin in 0.05 molar H3PMo12O40 solution under nitrogen in the presence of methanol gave no products whatsoever. It can consequently be assumed that the acyl radical shown in equations 11 and 12 results from the scission of the Cα-Cβ bond in the lignin.The formation of the CH3O. radical from methanol was also considered in more detail. The homolytic scission of the O-H bond in methanol is thermodynamically improbable owing to the high bond energy of 104 kcal/mol. It was, however, found that methanol in aqueous H3PMo12O40 solution under nitrogen is converted partly to dimethyl ether. The homolytic scission of the C-O bond in dimethyl ether is possible owing to the relatively low bond energy of 84 kcal/mol. It is consequently possible that methanol can form free radicals via acid-catalyzed ether formation and is thus considered to be a free-radical scavenger in the context of this invention. The direct addition of dimethyl ether as a free-radical scavenger for conversion of lignin in aqueous H3PMo12O40 solution under nitrogen and in the absence of methanol results in the production of a small amount of vanillic acid methyl ester. It was thus shown that dimethyl ether is directly active as a free-radical scavenger, and the homolytic scission of dimethyl ether and the associated formation of vanillic acid methyl ester is possible. In order to be able to compare the results of the degradation of lignin by means of POM and free-radical scavengers with the prior art, the method used by Wu et al. (benchmark) was applied to the lignin from Aldrich used in our examples.A comparison of the results revealed that the yield of lignin-based chemicals using the softwood lignin is very much lower compared to Wu et al. (one factor of ten). The reason for this may be the use of a very different lignin type. The lignin from Sigma-Aldrich used in our study is, according to the manufacturer, a typical softwood lignin which was isolated from spruce wood by means of the Kraft process. Wu et al. used, in contrast, a self-produced lignin type produced from hardwood by means of steam digestion. It is known that hardwood lignin has a very much higher proportion of syringyl units (50percent). The comparatively high proportion of syringyl units is also reflected in the results of Wu et al. in the considerable amount of syringaldehyde produced (7.8percent by weight). Softwood lignin (from the spruce) possesses, in contrast, a very great proportion of guaiacyl units (90percent). This corresponds with our results, in which only traces of syringaldehyde were formed. It is additionally known that the degradation of hardwood lignin proceeds very much more easily and rapidly than the degradation of softwood lignin. In addition, the hardwood lignin produced by Wu et al. was not characterized fully. The composition of the acid-insoluble lignin is reported by Wu et al. as: Klason lignin=84.7percent; acid-soluble lignin=3.0percent and others (unknown)=12.3percent.An economically viable process requires a reliable and inexpensive lignin source. It therefore appears to be advisable to use softwood lignin, which is obtainable in large amounts, as a starting material for chemical production. As already indicated, softwood lignin is obtained as a waste product in papermaking (for example in the Kraft or sulfite process). The method of Wu et al. is therefore applied below to the lignin available to us as a benchmark.A comparison of experiment 10 in which lignin was converted under oxygen in the presence of POM and free-radical scavenger with the prior art method (experiment 12) shows that a higher product yield is achieved with the inventive method. The chemicals produced are principally vanillin (16.5 mg) and vanillic acid methyl ester (13.5 mg).In experiment 11, poplar lignin was used. The product yield is likewise in the region of 3.5percent by weight. The main products here are, however, vanillin (5.0 mg), vanillic acid methyl ester (6.2 mg), syringaldehyde (8.2 mg) and syringic acid methyl ester (12.2 mg), corresponding to the chemical structure of poplar lignin with a relatively high proportion of syringyl units.It should be noted that the examples adduced in this document represent the first test series. The achievement of the comparatively higher yields is therefore particularly promising, since the inventive method has not yet been optimized. In view of the numerous possible combinations of POM, free-radical scavengers and ultimately also lignin types, there is still a very large amount of room for improvement of the yields. In addition, some reaction technology solutions, for example in situ extraction, are still available. The potential becomes clear in a comparison of experiments 06 and 10, among others. Here, the yield of chemicals was increased by a factor of 30 solely through the use of an aqueous methanol solution. One advantage of the invention presented here also lies in the possibility of preparing different chemicals depending on the free-radical scavenger. For instance, vanillic acid methyl ester is formed in the case of use of methanol, and vanillic acid ethyl ester in the case of use of ethanol. It consequently appears possible, through suitable combinations of POM and free-radical scavenger, to be able to crucially influence not just the yield but also the selectivity for a target product. TABLE 1 Results for production of chemicals from lignin by means of POM and free-radical scavenger compared to conventional methods. Products Experi- Catalytic Lignin [mg] percent by ment system Medium Gas type GC-MSwt.*) 01H3PMo12O40 H2ON2 Aldrich 0.56 0.06 (9.13 g) (100 ml) (10 bar) (1 g) 02H3PMo12O40 H2ON2 Aldrich 0.74 0.08 (9.13 g) (100 ml) (10 bar) (1 g) CHCl3 (30 ml) 03H3PMo12O40 H2ON2 Aldrich 1.17 0.13 (9.13 g) (60 ml) (10 bar) (1 g) C2H5OH (40 ml) 04H3PMo12O40 H2ON2 Aldrich 2.38 0.26 (9.13 g) (60 ml) (10 bar) (1 g) CH3OH (40 ml) 05Na3PMo12O40 H2OO2 Aldrich 1.47 0.16 (9.45 g) (100 ml) (5.1 bar) (1 g) 06H3PMo12O40 H2OO2 Aldrich 0.97 0.11 (9.13 g) (100 ml) (5.1 bar) (1 g) 07H3PMo12O40 H2OO2 Granit 0.59 0.06 (9.13 g) (100 ml) (5.1 bar) (1 g) 08H3PMo12O40 H2OO2 Aldrich 9.5 1.04 (9.13 g) (60 ml) (5.1 bar) (1 g) CH3OH (40 ml) 09H3PMo12O40 H2OO2 Aldrich 25.63 2.79 (9.13 g) (40 ml) (5.1 bar) (1 g) CH3OH (60 ml) 10H3PMo12O40 H2OO2 Aldrich 32.73 3.57 (9.13 g) (20 ml) (5.1 bar) (1 g) CH3OH (80 ml) 11H3PMo12O40 H2OO2 Poplar 34.22 3.64 (9.13 g) (20 ml) (5.1 bar) (1 g) CH3OH (80 ml) 12CuSO4/FeCl3 H2OO2 Aldrich 145 1.58 (0.5 g/0.05 g) (100 ml) (13.2 bar) (10 g) NaOH (12 g) Wu et al.CuSO4/FeCl3 H2OO2 Hardwood 12.9 (0.5 g/0.05 g) (100 ml) (13.8 bar) (10 g) NaOH (14.7 g) Blank noneH2ON2 Aldrich 0 0 sample (60 ml) (10 bar) (1 g) C2H5OH (40 ml) *)Based on dry lignin A

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With manganese(II) nitrate

T=100°C; P=6000.6 Torr; Ionic liquidAutoclave;

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Stärk, Kerstin; Taccardi, Nicola; Bösmann, Andreas; Wasserscheid, Peter

ChemSusChem, 2010 , vol. 3, # 6 p. 719 - 723 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 39573517 Find similar reactions

Stage #1: With oxygen

Stage #2: With formic acid; sodium formate in water

T=110°C; 24 h;

Rahimi, Alireza; Ulbrich, Arne; Coon, Joshua J.; Stahl, Shannon S.

Nature, 2014 , vol. 515, # 7526 p. 249 - 252 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 37471086 Find similar reactions

A: 83% B: 9%

With copper diacetate; oxygen-18

T=50°C; P=760.051 Torr; 8 h; Green chemistry;

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Jiang, Jian-An; Chen, Cheng; Huang, Jian-Gang; Liu, Hong-Wei; Cao, Song; Ji, Ya-Fei

Green Chemistry, 2014 , vol. 16, # 3 p. 1248 - 1254 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 37471087 Find similar reactions

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A: 27% B: 69%

With copper diacetate

T=50°C; 4 h; Green chemistry;

Jiang, Jian-An; Chen, Cheng; Huang, Jian-Gang; Liu, Hong-Wei; Cao, Song; Ji, Ya-Fei

Green Chemistry, 2014 , vol. 16, # 3 p. 1248 - 1254 Title/Abstract Full Text View citing articles Show Details

A: 26% B: 65%

With oxygen; cobalt(II) acetate; sodium hydroxide in water

T=50°C; P=760.051 Torr; 3 h; Green chemistry; Mechanism; regioselective reaction; Hide Experimental Procedure

Jiang, Jian-An; Du, Jia-Lei; Zhang, Zhong-Nan; Zhai, Jiao-Jiao; Ji, Ya-Fei

Synthetic Communications, 2014 , vol. 44, # 10 p. 1430 - 1440 Title/Abstract Full Text View citing articles Show Details

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2.3 Mechanistic studies (Scheme 2 in the text).

General procedure: Procedure for Scheme 2(a): mixture of substrate 1 (5.0 mmol), Co(OAc)2*4H2O (0.05 mmol, 12 mg)and NaOH (5.0 mmol, 0.2 g) in EG/H2O (5.0 mL/0.25 mL) was stirred with O2 (1.0 atm) being bubbled at 50 °C for 3 h. Hydrochloric acid (10.0 mL, 2 percent) and chloroform (10.0 mL) were successively added to reaction mixture. The chloroform phase was separated, and the aqueous phase was further extracted with chloroform (10.0 mL × 2). The combined organic layer was dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography on silica gel (eluents:petroleum ether/ethyl acetate, 5/1) to provide the intermediates 3 and desired products 2. A

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A: 5% B: 75%

With Ankistrodesmus braunii C202.7a

Microbiological reaction;

DellaGreca, Marina; Pinto, Gabriele; Pollio, Antonino; Previtera, Lucio; Temussi, Fabio

Tetrahedron Letters, 2003 , vol. 44, # 14 p. 2779 - 2780 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5317122 Find similar reactions

A: 4 % Chromat. B: 76 % Chromat.

With N-bromosuccinmide; zinc(II) chloride in tetrachloromethane

T=120°C; Arylation; 3 h;

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Baik, Woonphil; Lee, Hyun Joo; Jang, Jung Min; Koo, Sangho; Kim, Byeong Hyo

Journal of Organic Chemistry, 2000 , vol. 65, # 1 p. 108 - 115 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9116148 Find similar reactions

A: 3 % Chromat. B: 47 % Chromat. C: 47 % Chromat.

With oxygen; 4-methyl-4'-vinyl-2,2'-bipyridine in methanol

T=120°C; P=3040 Torr; 8 h;

Takaki, Ken; Shimasaki, Yohei; Shishido, Tetsuya; Takehira, Katsuomi

Bulletin of the Chemical Society of Japan, 2002 , vol. 75, # 2 p. 311 - 317 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 7448654 Find similar reactions

Richtzenhain

Chemische Berichte, 1944 , vol. 77/79, p. 409,416 Full Text View citing articles Show Details

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With horseradish peroxidase II; dihydrogen peroxide in phosphate buffer

T=30°C; pH=8; KineticsProduct distribution; Further Variations:pH-values;

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Fournand, David; Cathala, Bernard; Lapierre, Catherine

Phytochemistry, 2003 , vol. 62, # 2 p. 139 - 146 Title/Abstract Full Text View citing articles Show Details

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in water

T=121°C; Oxidation; P=750.06 Torr; 0.5 h;

Cai; Arntfield; Charlton

JAOCS, Journal of the American Oil Chemists' Society, 1999 , vol. 76, # 4 p. 433 - 441 Title/Abstract Full Text View citing articles Show Details