2,5-Dimethoxybenzaldehyde by Asch

Query Query

Results

Date

59 reactions in Reaxys

2016-05-19 11h:48m:19s (EST)

1. Query

Search as: As drawn

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Rx-ID: 2040179 View in Reaxys 1/59 Yield 100 %

Conditions & References With K2OsO4*2H2O, potassium carbonate, potassium hexacyanoferrate(III) in water, acetonitrile, Time= 0.75h, T= 60 °C , chemoselective reaction Fernandes, Rodney A.; Bethi, Venkati; RSC Advances; vol. 4; nb. 76; (2014); p. 40561 - 40568 View in Reaxys

99 %

With air, potassium carbonate in toluene, Time= 8h, T= 20 °C Lakshmi Kantam; Arundhathi; Likhar, Pravin R.; Damodara; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2633 - 2637 View in Reaxys

96 %

With aluminium trichloride, 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate, Time= 0.0166667h, Oxidation Hajipour, Abdol Reza; Mallakpour, Shadpour E.; Mohammadpoor-Baltork, Iraj; Khoee, Sepideh; Chemistry Letters; nb. 2; (2000); p. 120 - 121 View in Reaxys

95 %

With palladium diacetate, oxygen in dimethyl sulfoxide, Time= 12h, T= 80 °C Peterson, Karl P.; Larock, Richard C.; Journal of Organic Chemistry; vol. 63; nb. 10; (1998); p. 3185 - 3189 View in Reaxys

95 %

With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate in dichloromethane, Time= 0.0555556h, Microwave irradiation, Oxidation Hajipour, Abdol Reza; Mallakpour, Shadpour E.; Khoee, Sepideh; Synlett; nb. 5; (2000); p. 740 - 742 View in Reaxys

94 %

With Dess-Martin periodinane in dichloromethane, Time= 1h, T= 25 °C Dess, D. B.; Martin, J. C.; Journal of Organic Chemistry; vol. 48; nb. 22; (1983); p. 4155 - 4156 View in Reaxys

94 %

With potassium carbonate in toluene, Time= 12h, T= 20 °C Layek, Keya; Maheswaran; Arundhathi; Kantam, M. Lakshmi; Bhargava, Suresh K.; Advanced Synthesis and Catalysis; vol. 353; nb. 4; (2011); p. 606 - 616 View in Reaxys

93 %

With Dess-Martin periodinane in dichloromethane, Time= 0.333333h, Oxidation Parlow, John J.; Case, Brenda L.; South, Michael S.; Tetrahedron; vol. 55; nb. 22; (1999); p. 6785 - 6796 View in Reaxys

93 %

With 1,4-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane chlorochromate in acetonitrile, Time= 0.25h, Heating xxx; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 39; nb. 11; (2000); p. 863 - 866 View in Reaxys

92 %

With sodium nitrate, Time= 0.1h, T= 40 °C Hajipour, Abdol R.; Rafiee; Ruoho; Synlett; nb. 7; (2007); p. 1118 - 1120 View in Reaxys

92 %

With ammonium cerium (IV) nitrate, [HMIM][HSO4], Time= 0.333333h, T= 80 °C , neat (no solvent), chemoselective reaction Hajipour; Khazdooz; Ruoho; Journal of the Iranian Chemical Society; vol. 8; nb. 2; (2011); p. 382 - 387

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View in Reaxys 91 %

With tert -butyl hydrogen peroxide, titanium(IV) isopropylate in dichloromethane, Time= 24h, T= 20 °C Krohn, Karsten; Khanbabaee, Karamali; Rieger, Hagen; Chemische Berichte; vol. 123; nb. 6; (1990); p. 1357 1364 View in Reaxys

90 %

With aluminium trichloride, benzyltriphenylphosphonium periodate in acetonitrile, Time= 3.91667h, Heating Hajipour; Mallakpour; Samimi; Synlett; nb. 11; (2001); p. 1735 - 1738 View in Reaxys

90 %

With dipotassium peroxodisulfate, Time= 0.0833333h, T= 40 °C , Ionic liquid Chaskar; Bhandari; Patil; Sharma; Mayeker; Synthetic Communications; vol. 39; nb. 2; (2009); p. 366 - 370 View in Reaxys

88 %

With ammonium nitrate, hydrochlorid acid, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in water, acetonitrile, Time= 5h, T= 60 °C , Green chemistry Prebil, Rok; Stavber, Gaj; Stavber, Stojan; European Journal of Organic Chemistry; vol. 2014; nb. 2; (2014); p. 395 - 402 View in Reaxys

85 %

Oxidation Reactions; Typical Procedure General procedure: A solution of CAN (0.056 g, 0.102 mmoles) and sodium bromate (0.780 g, 5.17 mmoles) in H2O (3 mL) was added slowly to vigorously stirred anhydrous silica gel (5 g) that was contained in a 100 mLround-bottom flask containing a magnetic stirring bar and fitted with a rubber septum. After complete addition of the aqueous solution, stirring was continued until a free-flowing powder was obtained.CH2Cl2 (25 mL) was then added to the flask and a solution of hydroquinone 1A (220.23 mg, 2.0 mmol), in CH2Cl2 (5 mL) was added slowly to the stirred heterogeneous mixture. A condenser was attached to the flask and the reaction was heated to reflux. Disappearance of 1A was monitored by thin-layer chromatography (EtOAc–hexane, 1:4; panisaldehyde/sulfuric acid as staining agent). Upon complete disappearance of 1A (ca. 2 h), the reaction mixture was filtered through a sintered glass funnel, the solid residue was washed with additional CH2Cl2 (3 × 10 mL), and the washings were added to the filtrate. Removal of solvent from the organic solution under vacuum gave an orange solid. Radial chromatography of the crude product (EtOAc–hexane,1:9) gave 1,4-benzoquinone 2A (89 mg, 82percent) as an orange solid. With silica gel supported cerium(IV) ammonium nitrate-NaBrO3 in dichloromethane, water, Time= 2h, T= 40 °C Ali, Mohammed Hashmat; Welker, Andrea; York, Crystal; Synthesis (Germany); vol. 47; nb. 20; (2015); p. 3207 3211; Art.No: SS-2015-M0265-OP View in Reaxys

75 %

With potassium meta-periodate, tetraethylammonium bromide, Time= 0.0666667h, microwave irradiation Hajipour, Abdol Reza; Rafiee, Fatemeh; Ruoho, Arnold E.; Synthetic Communications; vol. 36; nb. 17; (2006); p. 2563 - 2568 View in Reaxys

50 %

With [(N,N-bis(2-pyridylmethyl)-N-bis(2-pyridyl)methylamine)oxoiron(IV)](ClO4)2 in acetonitrile, T= 24.84 °C , Kinetics Morimoto, Yuma; Park, Jiyun; Suenobu, Tomoyoshi; Lee, Yong-Min; Nam, Wonwoo; Fukuzumi, Shunichi; Inorganic Chemistry; vol. 51; nb. 18; (2012); p. 10025 - 10036 View in Reaxys

88 % Spectr.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, poly[4-(bis(acetoxy)iodo)]styrene, oxygen, KNO2, Time= 24h, T= 80 °C Herrerias, Clara I.; Zhang, Tony Y.; Li, Chao-Jun; Tetrahedron Letters; vol. 47; nb. 1; (2006); p. 13 - 17 View in Reaxys With cerium (IV) sulfate, AzBTS2- in sulfuric acid, acetonitrile, T= 25 °C , Kinetics, Thermodynamic data Branchi, Barbara; Galli, Carlo; Gentili, Patrizia; Organic and Biomolecular Chemistry; vol. 3; nb. 14; (2005); p. 2604 - 2614

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View in Reaxys With palladium diacetate, oxygen in dimethyl sulfoxide, T= 80 °C , p= 730Torr , Kinetics, Further Variations: var. catalyst concentration Steinhoff, Bradley A.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 128; nb. 13; (2006); p. 4348 - 4355 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, phen, oxygen, copper(II) sulfate in sodium hydroxide, Time= 5h, T= 100 °C , p= 7500.75Torr , pH= 13.5, Product distribution Figiel, Pawel J.; Leskelae, Markku; Repo, Timo; Advanced Synthesis and Catalysis; vol. 349; nb. 7; (2007); p. 1173 - 1179 View in Reaxys Reaction Steps: 2 1: 44 percent / TfOH / CH2Cl2 / 2 h / -5 °C 2: DDQ / CH2Cl2; H2O / Ambient temperature With triflic acid, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dichloromethane, water Wang, Wuyi; Li, Tiechao; Attardo, Giorgio; Journal of Organic Chemistry; vol. 62; nb. 19; (1997); p. 6598 - 6602 View in Reaxys Swern oxidation Teixeira, Robson R.; Barbosa, Luiz C. A.; Forlani, Giuseppe; Pilo-Veloso, Dorila; Carneiro, Jose Walkimar De Mesquita; Journal of Agricultural and Food Chemistry; vol. 56; nb. 7; (2008); p. 2321 - 2329 View in Reaxys > 95 %Spectr.

With phosphoric acid in water, toluene, Time= 24h, T= 25 °C , p= 760.051Torr , pH= 3.4, Irradiation, Inert atmosphere, Sealed tube Liu, Zijun; Caner, Joaquim; Kudo, Akihiko; Naka, Hiroshi; Saito, Susumu; Chemistry - A European Journal; vol. 19; nb. 29; (2013); p. 9452 - 9456 View in Reaxys With ammonium nitrate, hydrochlorid acid, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 5h, T= 60 °C , Green chemistry, chemoselective reaction Prebil, Rok; Stavber, Gaj; Stavber, Stojan; European Journal of Organic Chemistry; vol. 2014; nb. 2; (2014); p. 395 - 402 View in Reaxys

O O

Rx-ID: 8841028 View in Reaxys 2/59 Yield 95 %

Conditions & References With aluminium trichloride, tetramethylammonium chlorochromate in acetonitrile, Time= 1.08333h, Heating Hajipour, Abdol R.; Ruohol, Arnold E.; Synthetic Communications; vol. 33; nb. 6; (2003); p. 871 - 878 View in Reaxys

80 %

With bismuth(III) chloride, benzyltriphenylphosphonium peroxymonosulfate in dichloromethane, Time= 0.0583333h, microwave irradiation Hajipour; Mallakpour; Baltork; Adibi; Synthetic Communications; vol. 31; nb. 11; (2001); p. 1625 - 1631 View in Reaxys

75 %

With bismuth(III) chloride, benzyltriphenylphosphonium peroxymonosulfate in acetonitrile, Time= 0.5h, Heating

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Hajipour; Mallakpour; Mohammadpoor-Baltork; Adibi; Phosphorus, Sulfur and Silicon and Related Elements; vol. 165; (2000); p. 155 - 163 View in Reaxys 75 %

With benzyltriphenylphosphonium chlorate, aluminium trichloride in acetonitrile, Time= 8h, Heating Hajipour, Abdol Reza; Mallakpour, Shadpour E; Mohammadpoor-Baltork, Iraj; Malakoutikhah, Morteza; Tetrahedron; vol. 58; nb. 1; (2002); p. 143 - 146 View in Reaxys

75 %

With aluminium trichloride, benzyltriphenylphosphonium chlorochromate in acetonitrile, Time= 0.5h, Heating Hajipour; Mallakpour; Baltork; Backnezhad; Organic Preparations and Procedures International; vol. 34; nb. 2; (2002); p. 169 - 175 View in Reaxys

O HO

Rx-ID: 9394373 View in Reaxys 3/59 Yield

Conditions & References

91 %

With 2-iodoxybenzoic acid, β-cyclodextrin in water, acetone, Time= 12h, T= 20 °C Krishnaveni, N. Srilakshmi; Surendra; Nageswar; Rao, K. Rama; Synthesis; nb. 13; (2003); p. 1968 - 1970 View in Reaxys

90 %

With iodobenzene, β-cyclodextrin, potassium bromide in water, acetone, Time= 12h, T= 20 °C Narender; Somi Reddy; Srilakshmi Krishnaveni; Surendra; Nageswar; Rama Rao; Synthetic Communications; vol. 36; nb. 10; (2006); p. 1463 - 1470 View in Reaxys

80 %

With N-bromosuccinmide, β-cyclodextrin in water, acetone, Time= 0.333333h, T= 20 °C Reddy, M. Somi; Narender; Rao, K. Rama; Synthetic Communications; vol. 34; nb. 21; (2004); p. 3875 - 3881 View in Reaxys

O O

Rx-ID: 32863988 View in Reaxys 4/59 Yield

Conditions & References 4.7. (R)-(+)-Acetoxy-2,5-dimethoxyphenylacetonitrile (R)-5 Racemic acetoxy-2,5-dimethoxyphenylacetonitrile (1.00 g, 4.25 mmol) was suspended in toluene (12 mL) in a screwcap conical flask and 0.1 M pH 7 potassium phosphate buffer (17 mL) followed by C. antarctica B (381 mg, 38percent w/w) were added. The mixture was shaken at 35 °C at 750 rpm for 118 h. After sonication it was filtered through Celite.(R). and the pad was washed successively with diethyl ether (30 mL), water (25 mL) and ether (30 mL). The filtrate was transferred to a separating funnel and without shaking the organic phase was removed. The aqueous phase was extracted with ether (1 .x. 30 mL) and the combined organic extracts were dried and concentrated in vacuo to afford the crude product mixture as an oil (0.78 g). Column chromatography (dichloromethane) provided an approximate 3:1 mixture of the unhydrolysed ester and the aldehyde (0.51 g). With Candida antarctica lipase B in toluene, Time= 118h, T= 35 °C , aq. phosphate buffer, Enzymatic reaction Maguire, Nuala M.; Ford, Alan; Clarke, Sarah L.; Eccles, Kevin S.; Lawrence, Simon E.; Brossat, Maude; Moody, Thomas S.; Maguire, Anita R.; Tetrahedron Asymmetry; vol. 22; nb. 24; (2011); p. 2144 - 2150 View in Reaxys

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O O

O O O

Rx-ID: 33465247 View in Reaxys 5/59 Yield

Conditions & References

7 %, 32 %

4.2. Typical procedure for one-pot conversion of aromatic bromides into aromatic ethyl esters with ethyl formate General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of pbromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil. Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 2h, T= 0 °C Stage 2: in tetrahydrofuran, hexane, Time= 3h, T= -78 °C Stage 3: With ethanol, iodine, potassium carbonate in tetrahydrofuran, hexane, Time= 14h, T= -78 - 20 °C Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 68; nb. 24; (2012); p. 4701 - 4709 View in Reaxys

–O

S O

K+

Rx-ID: 23834917 View in Reaxys 6/59 Yield 88.3 %

Conditions & References 5 :A slurry of 21.7 g of the potassium salt (90 wt percent assay, 0.103 moles), 100 mL of acetone, and 15 g (0.119 moles) of dimethyl sulfate was warmed to 35-40° C. and held at that temperature for 2 hours at which point an analysis by TLC indicated that the reaction was complete. The resulting slurry was drowned into 300 mL of water and the resulting light yellow crystals were filtered off, washed with water, and air-dried. The weight of product was 15.1 g (88.3percent yield); both the HPLC area and the HPLC weight percents were 100 in acetone, Time= 2h, T= 35 - 40 °C , Product distribution / selectivity Patent; Shanks, Thomas Elbert; Maleski, Robert Joseph; US2003/199714; (2003); (A1) English View in Reaxys

70 %

7 :A slurry of 19.0 g of potassium salt (90 wt percent assay, 0.09 moles), 65 g of isopropyl alcohol, 0.1 g of tetrabutylammonium bromide, and 13.9 g (0.11 moles) of dimethyl sulfate was warmed to 35-40° C. and held for 30 minute at which time an analysis by TLC indicated that the reaction was complete. The resulting slurry was treated with 65 g of water and the product slurry was cooled to 20° C. The product was collected by filtration and washed with 50percent aqueous isopropyl alcohol, and dried. The product weight was 10.9 g (70percent yield). Its HPLC area percent assay was 99.9percent; weight percent was 97.5percent With tetrabutylammomium bromide in isopropyl alcohol, Time= 0.5h, T= 35 - 40 °C , Product distribution / selectivity Patent; Shanks, Thomas Elbert; Maleski, Robert Joseph; US2003/199714; (2003); (A1) English View in Reaxys

62 %

6 :A slurry of 21.0 g of potassium salt (90 wt percent assay, 0.103 moles), 81 g of heptane, 6 g of DMF, and 18.9 g (0.15 moles) of dimethyl sulfate was refluxed for 30 minutes at which point an analysis by TLC indicated that the reaction was complete. The resulting slurry was cooled to 50° C. and treated with 25 mL of water and 15 mL of concentrated HCl. The water phase was decanted and the product was crystallized by cooling to room temperature. After cooling to 0° C. the product was collected by filtration, washed with heptane, and dried to give 10.2 g (62percent yield) of light yellow solid. Both the HPLC area and the HPLC weight percents were 100 in n-heptane, N,N-dimethyl-formamide, Time= 0.5h, Heating / reflux, Product distribution / selectivity

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Patent; Shanks, Thomas Elbert; Maleski, Robert Joseph; US2003/199714; (2003); (A1) English View in Reaxys

O O

Cl O

Rx-ID: 10231659 View in Reaxys 7/59 Yield

Conditions & References

100 %

With titanium tetrachloride in dichloromethane, T= 0 °C Piggott, Matthew J.; Wege, Dieter; Tetrahedron; vol. 62; nb. 15; (2006); p. 3550 - 3556 View in Reaxys With titanium tetrachloride in dichloromethane, Time= 0.25h, T= 20 °C Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200 View in Reaxys

S O

O O

Rx-ID: 753195 View in Reaxys 8/59 Yield

Conditions & References

77 - 82 %

1(a); 1(b) :The above crude oil (6.1 g, 81percent assay, 0.33 moles), 25 mL of acetone, 6.8 g of potassium carbonate, and 5 g of dimethylsulfate was refluxed for 3 hours and drowned into 200 mL of water. The dark oil solidified overnight, and the product was collected by filtration and dried to yield 5.6 g of black solid. The weight percent assay was 83percent, resulting in an assay yield of 77percent. The liquid chromatograph area percentage was only 62percent; The oil from Example 1 was distilled at 10 mm through a 6-inch Vigreaux column. A light yellow fraction boiling at 124-129° C. was collected. The liquid chromatograph area percentage was 95percent and the liquid chromatographic weight percentage was 90percent. The overall assay yield based on the starting 4-methoxyphenol was 70percent. The distilled oil was then converted to 2,5-dimethoxybenzaldehyde via the procedure in Comparative Example 1(a). An 82percent yield of light yellow crystals having a liquid chromatograph weight percent assay of 99.3percent was obtained With potassium carbonate in acetone, Time= 3h, Heating / reflux, Product distribution / selectivity Patent; Shanks, Thomas Elbert; Maleski, Robert Joseph; US2003/199714; (2003); (A1) English View in Reaxys With sodium hydroxide Neuberger; Biochemical Journal; vol. 43; (1948); p. 599,602 View in Reaxys With sodium hydroxide in water, Time= 0.5h, T= 65 °C , Yield given Chu, Kwong Yung; Griffiths, John; Ward, David; Journal of Chemical Research, Miniprint; nb. 10; (1981); p. 3701 - 3721 View in Reaxys

O O

O S

Rx-ID: 9467890 View in Reaxys 9/59 Yield 90 %

Conditions & References With 2,4,6-trichloro-1,3,5-triazine, dimethyl sulfoxide in dichloromethane, Time= 1h, T= 20 °C

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Karimi, Babak; Hazarkhani, Hassan; Synthesis; nb. 16; (2003); p. 2547 - 2551 View in Reaxys

O O

Rx-ID: 9741091 View in Reaxys 10/59 Yield

Conditions & References

89 %

With sulfuric acid, 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, Time= 5h, T= 80 °C Branytska, Oiena; Neumann, Ronny; Synlett; nb. 9; (2004); p. 1575 - 1576 View in Reaxys

O O

HO O

Rx-ID: 3133096 View in Reaxys 11/59 Yield

Conditions & References

95 %, 16 %

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, water, Time= 2.5h, T= 20 °C Nakajima, Noriyuki; Abe, Reiko; Yonemitsu, Osamu; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4244 - 4247 View in Reaxys

O Si

Rx-ID: 9979285 View in Reaxys 12/59 Yield

Conditions & References

72 %

With N-bromosuccinmide, β-cyclodextrin in ethyl acetate, acetone, Time= 7h, T= 20 °C Reddy, M. Somi; Narender; Nageswar; Rao, K. Rama; Synthesis; nb. 5; (2005); p. 714 - 716; Art.No: Z20704SS View in Reaxys O

Rx-ID: 29899771 View in Reaxys 13/59 Yield

Conditions & References

89 %

With sodium azide, [bis(acetoxy)iodo]benzene in acetonitrile, Time= 0.25h, T= 0 - 20 °C Telvekar, Vikas N.; Sasane, Kulbhushan A.; Synlett; nb. 18; (2010); p. 2778 - 2780 View in Reaxys

O O

Rx-ID: 2209534 View in Reaxys 14/59

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Yield

Conditions & References

100 %

With [NO(1+)*18-crown-6*H(NO3)2(1-)], silica gel in dichloromethane, Time= 0.0833333h, T= 20 °C Zolfigol, Mohammad Ali; Zebarjadian, Mohammad Hassan; Mohammadpoor-Baltork, Iraj; Shamsipur, Mojtaba; Synthetic Communications; vol. 32; nb. 18; (2002); p. 2803 - 2808 View in Reaxys

99 %

With bismuth(III) chloride in chloroform, Time= 0.166667h, Heating, deprotection Mohammadpoor-Baltork; Aliyan; Synthetic Communications; vol. 29; nb. 16; (1999); p. 2741 - 2746 View in Reaxys

99 %

With aluminium trichloride in acetonitrile, Time= 0.05h, Heating, Deacetylation Mohammadpoor-Baltork, Iraj; Aliyan, Hamid; Journal of Chemical Research - Part S; nb. 4; (1999); p. 272 - 273 View in Reaxys

99 %

With tin(ll) chloride in acetonitrile, Time= 0.0333333h, T= 25 °C , Hydrolysis Mohammadpoor-Baltork; Aliyan; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 10; (1999); p. 1223 - 1225 View in Reaxys

99 %

With water, TiF4, Time= 5h, T= 60 °C , screw-capped vial Jung, Misuk; Yoon, Jieun; Kim, Hak Sung; Ryu, Jae-Sang; Synthesis; nb. 16; (2010); p. 2713 - 2720; Art.No: F04310SS View in Reaxys

96 %

With 2,6-dicarboxypyridinium chlorochromate in acetonitrile, Time= 0.0833333h, T= 20 °C Hosseinzadeh, Rahman; Tajbakhsh, Mahmood; Shakoori, Alireza; Niaki, Mohammad Yazdani; Monatshefte fur Chemie; vol. 135; nb. 10; (2004); p. 1243 - 1249 View in Reaxys

95 %

With tetrachlorosilane in dichloromethane, Time= 0.25h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Hazarkhani, Hassan; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 177; nb. 12; (2002); p. 2847 - 2858 View in Reaxys

94 %

With aluminum oxide, Time= 0.00833333h, T= 35 °C , microwave irradiation Varma, Rajender S.; Chatterjee, Arnab K.; Varma, Manju; Tetrahedron Letters; vol. 34; nb. 20; (1993); p. 3207 3210 View in Reaxys

92 %

With cerium(IV) ammonium nitrate supported on silica in dichloromethane, Time= 0.25h Cotelle, Philippe; Catteau, Jean-Pierre; Tetrahedron Letters; vol. 33; nb. 27; (1992); p. 3855 - 3858 View in Reaxys

92 %

With cerium(IV) ammonium nitrate supported on silica in dichloromethane, Time= 0.25h, other benzaldehyde diacetates Cotelle, Philippe; Catteau, Jean-Pierre; Tetrahedron Letters; vol. 33; nb. 27; (1992); p. 3855 - 3858 View in Reaxys 2H

O Cl

O 2H

2H 2H

2H 2

O 2H 2H

O 2H

Rx-ID: 11154050 View in Reaxys 15/59

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Yield

Conditions & References

73 %

With titanium tetrachloride in dichloromethane, Time= 0.25h, T= 20 °C Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 2; (2007); p. 493 - 502 View in Reaxys

73 %

With titanium tetrachloride in dichloromethane, Time= 0.25h, T= 20 °C Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200 View in Reaxys

KBr3

Rx-ID: 24880428 View in Reaxys 16/59 Yield

Conditions & References 1 : EXAMPLE 1 EXAMPLE 1 Pursuant to this invention 2-bromo-1,4-dimethoxybenzene, a useful intermediate for the synthesis of the pharmaceutical intermediate 2,5-dimethoxybenzaldehyde, was produced in the following manner: Into a 500 mL round bottom flask were charged 100 grams of 1,4-dimethoxybenzene and 100 grams of methylene dibromide. An endotherm to 12° C. occurred when creating this solution. Separately prepared was a solution of 90 grams of KBr in 265 grams of water to which was added 35.5 mL of bromine, and the resulting mixture was stirred to form an aqueous solution of KBr3. A portion of this solution (250 mL) was added slowly to the 1,4-dimethoxybenzene solution. After a slight exotherm from 13° to 22° C. occurred (in 20 minutes) a cooling water bath was applied externally to the flask to keep the temperature at 22°-25° C. The total feed time was 70 minutes. The bromine color disappeared within 10 minutes after the addition had been completed. To dissolve some salts that appeared in the reaction mixture, 60 mL of water was added thereto. The phases were separated in a separatory funnel and the aqueous layer was discarded. The organic phase was washed with 30 grams of 10percent sodium carbonate solution (pH 7-10) and the phases separated readily. The product solution was stripped at reduced pressure to 65° C. at 0.5 mm Hg pressure, distilled and subjected to analysis. With bromine, sodium carbonate, potassium bromide in water Patent; Ethyl Corporation; US4940807; (1990); (A1) English View in Reaxys H

O Cl

H 13C O

13C

13CH

H 13C O

13C

13C 13C

O O

Rx-ID: 38014831 View in Reaxys 17/59 Yield 91 %

Conditions & References With titanium tetrachloride in dichloromethane, Time= 17h, T= -5 - 4 °C , Inert atmosphere, Rieche Formylation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys

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O OH

Rx-ID: 28927772 View in Reaxys 18/59 Yield

Conditions & References

99 %, 2 %

With air, potassium carbonate, Time= 16h, T= 20 °C Lakshmi Kantam; Arundhathi; Likhar, Pravin R.; Damodara; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2633 - 2637 View in Reaxys

Rx-ID: 28927774 View in Reaxys 19/59 Yield

Conditions & References

99 %, 10 %

With air, potassium carbonate, Time= 8h, T= 20 °C Lakshmi Kantam; Arundhathi; Likhar, Pravin R.; Damodara; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2633 - 2637 View in Reaxys

O H

OHO

racemate

Rx-ID: 4802301 View in Reaxys 20/59 Yield

Conditions & References

30 %, 23 %

With manganese(IV) oxide in dichloromethane, Time= 5h, T= 21 °C , other reagent PDC Shiue, Jiann-Shyng; Lin, Mei-Huey; Fang, Jim-Min; Journal of Organic Chemistry; vol. 62; nb. 14; (1997); p. 4643 - 4649 View in Reaxys

O O O

racemate

Rx-ID: 4803341 View in Reaxys 21/59 Yield 18 %, 12 %

Conditions & References With potassium tert-butylate in tetrahydrofuran, Time= 18h, T= 25 °C Shiue, Jiann-Shyng; Lin, Mei-Huey; Fang, Jim-Min; Journal of Organic Chemistry; vol. 62; nb. 14; (1997); p. 4643 - 4649 View in Reaxys

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O O

Rx-ID: 8838841 View in Reaxys 22/59 Yield

Conditions & References

88 %

With aluminum oxide, potassium permanganate, Time= 0.25h, Product distribution, Further Variations: Reagents, reaction times Hajipour; Mallakpour; Baltork; Backnezhad; Synthetic Communications; vol. 32; nb. 5; (2002); p. 771 - 779 View in Reaxys

88 %

With aluminium trichloride, tetramethylammonium chlorochromate in acetonitrile, Time= 1h, Heating Hajipour, Abdol R.; Ruohol, Arnold E.; Synthetic Communications; vol. 33; nb. 6; (2003); p. 871 - 878 View in Reaxys

85 %

With bismuth(III) chloride, benzyltriphenylphosphonium peroxymonosulfate in dichloromethane, Time= 0.0666667h, microwave irradiation Hajipour; Mallakpour; Baltork; Adibi; Synthetic Communications; vol. 31; nb. 11; (2001); p. 1625 - 1631 View in Reaxys

78 %

With bismuth(III) chloride, benzyltriphenylphosphonium peroxymonosulfate in acetonitrile, Time= 1.5h, Heating Hajipour; Mallakpour; Mohammadpoor-Baltork; Adibi; Phosphorus, Sulfur and Silicon and Related Elements; vol. 165; (2000); p. 155 - 163 View in Reaxys

78 %

With aluminium trichloride, benzyltriphenylphosphonium chlorochromate in acetonitrile, Time= 1.5h, Heating Hajipour; Mallakpour; Baltork; Backnezhad; Organic Preparations and Procedures International; vol. 34; nb. 2; (2002); p. 169 - 175 View in Reaxys

48 %

With aluminium trichloride, benzyltriphenylphosphonium chlorate in acetonitrile, Time= 9h, T= 20 °C Hajipour, Abdol Reza; Mallakpour, Shadpour E; Mohammadpoor-Baltork, Iraj; Malakoutikhah, Morteza; Tetrahedron; vol. 58; nb. 1; (2002); p. 143 - 146 View in Reaxys

H N

O O

NH 2 O

Rx-ID: 8878223 View in Reaxys 23/59 Yield

Conditions & References

96 %

With aluminium trichloride, 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate, Time= 0.0108333h, T= 20 °C Hajipour; Mallakpour; Mohammadpoor-Baltork; Khoee; Synthetic Communications; vol. 31; nb. 8; (2001); p. 1187 - 1194 View in Reaxys

–O

O O

Na +

S O

O O

Rx-ID: 23834918 View in Reaxys 24/59

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Yield

Conditions & References

88.3 %

8 :A slurry of 7.87 g of sodium salt (73 wt percent assay, 0.033 moles), 25 mL of acetone, and 5 g (0.04 moles) of dimethyl sulfate was refluxed for 3 hours at which time an analysis by TLC indicated that the reaction was complete. The resulting slurry was drowned into 200 mL of water and the resulting light yellow crystals were filtered off, washed with water, and air-dried. The weight of product was 5.1 g (88.3percent yield). The HPLC weight percent was 92.5, area percent was 96 in acetone, Time= 3h, Heating / reflux, Product distribution / selectivity Patent; Shanks, Thomas Elbert; Maleski, Robert Joseph; US2003/199714; (2003); (A1) English View in Reaxys

Rx-ID: 8644965 View in Reaxys 25/59 Yield

Conditions & References

16 %, 37 %

With dipyridinium dichromate, 3 A molecular sieve, acetic acid in dichloromethane, Time= 1.5h, T= 20 °C , Oxidation Gill, Melvyn; Harte, Michael F.; Ten, Abilio; Australian Journal of Chemistry; vol. 53; nb. 4; (2000); p. 245 - 256 View in Reaxys

I OH

Rx-ID: 840211 View in Reaxys 26/59 Yield

Conditions & References With potassium hydroxide Waljaschko; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 58; (1926); p. 795; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 1125 View in Reaxys With potassium carbonate in acetone, Time= 20h, T= 25 °C Ravi Kumar; Behera, Manoranjan; Raghavulu; Jaya Shree; Yennam, Satyanarayana; Tetrahedron Letters; vol. 53; nb. 32; (2012); p. 4108 - 4113 View in Reaxys

O O

Rx-ID: 3612763 View in Reaxys 27/59 Yield 55 %

Conditions & References With lead(IV) acetate in benzene, Heating Shankaran, K.; Rao, A.S.; Synthetic Communications; vol. 10; nb. 7; (1980); p. 573 - 580 View in Reaxys

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2H 2H

O 2H 2H

O 2H

Rx-ID: 11382610 View in Reaxys 28/59 Yield

Conditions & References Reaction Steps: 2 1.1: KOH / tetrabutylammonium bromide / 20 °C 1.2: 98 percent / 72 h / 40 - 45 °C 2.1: 73 percent / titanium tetrachloride / CH2Cl2 / 0.25 h / 20 °C With potassium hydroxide, titanium tetrachloride, tetrabutylammomium bromide in dichloromethane Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 2; (2007); p. 493 - 502 View in Reaxys

O O

Rx-ID: 28484117 View in Reaxys 29/59 Yield

Conditions & References With ammonium cerium (IV) nitrate in water, acetonitrile, T= 20 °C Love, Brian E.; Bonner-Stewart, Jeffrey; Forrest, Lori A.; Synlett; nb. 5; (2009); p. 813 - 817 View in Reaxys

Rx-ID: 4793666 View in Reaxys 30/59 Yield

Conditions & References With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, water, Ambient temperature Wang, Wuyi; Li, Tiechao; Attardo, Giorgio; Journal of Organic Chemistry; vol. 62; nb. 19; (1997); p. 6598 - 6602 View in Reaxys

O O

Rx-ID: 18857526 View in Reaxys 31/59 Yield

Conditions & References Reaction Steps: 3 1: polyphosphoric acid 2: 96 percent / sodium borohydride / ethanol 3: 55 percent / lead tetraacetate / benzene / Heating With lead(IV) acetate, sodium tetrahydroborate, PPA in ethanol, benzene Shankaran, K.; Rao, A.S.; Synthetic Communications; vol. 10; nb. 7; (1980); p. 573 - 580 View in Reaxys Reaction Steps: 3 1: AlCl3

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2: 96 percent / sodium borohydride / ethanol 3: 55 percent / lead tetraacetate / benzene / Heating With lead(IV) acetate, sodium tetrahydroborate, aluminium trichloride in ethanol, benzene Shankaran, K.; Rao, A.S.; Synthetic Communications; vol. 10; nb. 7; (1980); p. 573 - 580 View in Reaxys Reaction Steps: 2 1: 85 percent Bergman, Jan; Renstroem, Lars; Sjoeberg, Birger; Tetrahedron; vol. 36; (1980); p. 2505 - 2512 View in Reaxys

O O

zinc cyanide

Rx-ID: 5857321 View in Reaxys 32/59 Yield

Conditions & References With hydrogenchloride, aluminium trichloride, benzene, T= 50 °C , und Kochen des Reaktionsproduktes mit verd.Salzsaeure Gulland; Virden; Journal of the Chemical Society; (1928); p. 1482 View in Reaxys

Rx-ID: 18826117 View in Reaxys 33/59 Yield

Conditions & References Reaction Steps: 2 1: 96 percent / sodium borohydride / ethanol 2: 55 percent / lead tetraacetate / benzene / Heating With lead(IV) acetate, sodium tetrahydroborate in ethanol, benzene Shankaran, K.; Rao, A.S.; Synthetic Communications; vol. 10; nb. 7; (1980); p. 573 - 580 View in Reaxys

O O

O HO

O O

Rx-ID: 34035802 View in Reaxys 34/59 Yield

Conditions & References

10 %, 30 %

With [(N,N-bis(2-pyridylmethyl)-N-bis(2-pyridyl)methylamine)oxoiron(IV)](ClO4)2, scandium tris(trifluoromethanesulfonate) in acetonitrile, T= 24.84 °C , Kinetics Morimoto, Yuma; Park, Jiyun; Suenobu, Tomoyoshi; Lee, Yong-Min; Nam, Wonwoo; Fukuzumi, Shunichi; Inorganic Chemistry; vol. 51; nb. 18; (2012); p. 10025 - 10036 View in Reaxys

H 13C 13CH O

H 13C 13CH

H 13C O

13C

13C 13C

O O

Rx-ID: 38014757 View in Reaxys 35/59

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Yield

Conditions & References Reaction Steps: 3 1: N-bromosuccinmide / chloroform; N,N-dimethyl-formamide / 70 °C 2: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 3: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere With N-bromosuccinmide, copper(l) iodide, titanium tetrachloride, ethyl acetate in methanol, dichloromethane, chloroform, N,N-dimethyl-formamide, 3: |Rieche Formylation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H

H 13C 13CH HO 13C

H 13C

13CH

13C

H 13C 13CH

C H

Rx-ID: 38014778 View in Reaxys 36/59 Yield

Conditions & References Reaction Steps: 4 1.1: sodium hydroxide / water / 0.5 h / |Inert atmosphere 1.2: 1 h / 0 - 50 °C / |Inert atmosphere 2.1: N-bromosuccinmide / chloroform; N,N-dimethyl-formamide / 70 °C 3.1: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 4.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere With N-bromosuccinmide, copper(l) iodide, titanium tetrachloride, ethyl acetate, sodium hydroxide in methanol, dichloromethane, chloroform, water, N,N-dimethyl-formamide, 4.1: |Rieche Formylation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H

H 13C 13C

13C

H C

13C

H 13C

13CH

13C

Rx-ID: 38014788 View in Reaxys 37/59 Yield

Conditions & References Reaction Steps: 2 1: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 2: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere With copper(l) iodide, titanium tetrachloride, ethyl acetate in methanol, dichloromethane, N,N-dimethyl-formamide, 2: |Rieche Formylation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys

O O

N O

OH O

O N

Rx-ID: 3676728 View in Reaxys 38/59 Yield

Conditions & References With ammonium cerium(IV) nitrate, water in acetonitrile, Time= 2h, Ambient temperature, Title compound not separated from byproducts Badea; Cotelle; Catteau; Synthetic Communications; vol. 24; nb. 14; (1994); p. 2011 - 2016 View in Reaxys

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2.5-dimethoxy-phenyl magnesium bromide

N O

Rx-ID: 5857320 View in Reaxys 39/59 Yield

Conditions & References With diethyl ether, und anschliessend mit wss.H2SO4 Smith; Bayliss; Journal of Organic Chemistry; vol. 6; (1941); p. 437,440 View in Reaxys

O O

Rx-ID: 796559 View in Reaxys 40/59 Yield

Conditions & References With aluminium trichloride, benzene, man erhitzt dann auf 35-40grad und leitet 4 Stdn. HCl durch die Fluessigkeit; man zersetzt das Reaktionsprodukt erst mit Eiswasser, dann durch Destillation mit Wasserdampf Gattermann; Justus Liebigs Annalen der Chemie; vol. 357; (1907); p. 373 View in Reaxys Kauffmann; Chemische Berichte; vol. 40; (1907); p. 840 View in Reaxys Kauffmann; Burr; Chemische Berichte; vol. 40; (1907); p. 2357 View in Reaxys

O O

Rx-ID: 3346119 View in Reaxys 41/59 Yield

Conditions & References With sodium hydroxide, diphosphoric acid tetrachloride, 1) 100 deg C, 48 h, Yield given. Multistep reaction Downie, Ian M.; Earle, Martyn J.; Heaney, Harry; Shuhaibar, Khamis F.; Tetrahedron; vol. 49; nb. 19; (1993); p. 4015 - 4034 View in Reaxys

E N O

O O

Rx-ID: 4538321 View in Reaxys 42/59 Yield

Conditions & References With hydrogenchloride, n-butyllithium, methyl iodide, 1) ether, hexane, rt, 1 h; 2) ether, hexane, -65 deg C, rt, 1 h; 3) THF, reflux, 1.5 h, Yield given. Multistep reaction. Yields of byproduct given Flippin, Lee A.; Berger, Jacob; Parnes, Jason S.; Gudiksen, Mark S.; Journal of Organic Chemistry; vol. 61; nb. 14; (1996); p. 4812 - 4815 View in Reaxys

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zinc O

Rx-ID: 19499764 View in Reaxys 43/59 Yield

Conditions & References Reaction Steps: 2 1: 2.4 g / K2S2O8 2: methylation With dipotassium peroxodisulfate Iinuma; Iwashima; Matsuura; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 12; (1984); p. 4935 - 4941 View in Reaxys

Rx-ID: 22064072 View in Reaxys 44/59 Yield

Conditions & References Reaction Steps: 2 1: potassium persulfate; NaOH-solution; alkali / 30 - 35 °C / und Erhitzen des Reaktionsprodukts mit konz.Salzsaeure auf 70grad 2: aqueous NaOH-solution With sodium hydroxide, potassium peroxomonosulphate Hodgson; Beard; Journal of the Chemical Society; (1927); p. 2340 View in Reaxys Reaction Steps: 2 1: potassium persulfate; NaOH-solution; alkali / 30 - 35 °C / und Erhitzen des Reaktionsprodukts mit konz.Salzsaeure auf 70grad 2: aqueous NaOH-solution With sodium hydroxide, potassium peroxomonosulphate Hodgson; Beard; Journal of the Chemical Society; (1927); p. 2340 View in Reaxys

O HO

Rx-ID: 157704 View in Reaxys 45/59 Yield

Conditions & References With potassium permanganate Schnell; Chemische Berichte; vol. 17; (1884); p. 1387 View in Reaxys

O O

O Cl

Rx-ID: 320552 View in Reaxys 46/59 Yield

Conditions & References With quinoline, Pd-BaSO4, sulfur, Hydrogenation.Reagens 4: Xylol Alberti; Cattapan; ; vol. 91; (1957); p. 13,23

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View in Reaxys

S O

O O

Rx-ID: 753284 View in Reaxys 47/59 Yield

Conditions & References With sodium hydroxide Hirai; Biochemische Zeitschrift; vol. 189; (1927); p. 90 View in Reaxys Hodgson; Beard; Journal of the Chemical Society; (1927); p. 2340 View in Reaxys

E N O

O O

Rx-ID: 4510593 View in Reaxys 48/59 Yield

Conditions & References With hydrogenchloride, methyl iodide, 1) ether, hexane, rt, 1 h; 2) ether, hexane, -65 deg C, rt, 1 h; 3) THF, reflux, 1.5 h, Yield given. Multistep reaction. Yields of byproduct given Flippin, Lee A.; Berger, Jacob; Parnes, Jason S.; Gudiksen, Mark S.; Journal of Organic Chemistry; vol. 61; nb. 14; (1996); p. 4812 - 4815 View in Reaxys

E N O

O O

Rx-ID: 4554179 View in Reaxys 49/59 Yield

Conditions & References With hydrogenchloride, n-butyllithium, 1) ether, hexane, rt, 1 h; 2) ether, hexane, -65 deg C, rt, 1 h; 3) THF, reflux, 1.5 h, Yield given. Multistep reaction. Yields of byproduct given Flippin, Lee A.; Berger, Jacob; Parnes, Jason S.; Gudiksen, Mark S.; Journal of Organic Chemistry; vol. 61; nb. 14; (1996); p. 4812 - 4815 View in Reaxys

O O

Rx-ID: 656298 View in Reaxys 50/59

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Yield

Conditions & References With aluminium trichloride, Verseifen des gebildeten Esters, Kochen der 2.5-Dimethoxy-phenylglyoxylsaeure mit Anilin und Zerzetzen des so enstehenden <2.5-Dimethoxy-benzal>-anilins mit verd. Schwefelsaeure Bouveault; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 122; (1896); p. 1545; Bulletin de la Societe Chimique de France; vol. <3>17; (1897); p. 947 View in Reaxys

I O O

Rx-ID: 840090 View in Reaxys 51/59 Yield

Conditions & References With sodium methylate Tiemann; Mueller; Chemische Berichte; vol. 14; (1881); p. 1986 View in Reaxys

S O

Rx-ID: 753285 View in Reaxys 52/59 Yield

Conditions & References With sodium hydroxide Hodgson; Beard; Journal of the Chemical Society; (1927); p. 2340 View in Reaxys

O O

F F

O N

O O

F F

Rx-ID: 3006063 View in Reaxys 53/59 Yield

Conditions & References Bergman, Jan; Renstroem, Lars; Sjoeberg, Birger; Tetrahedron; vol. 36; (1980); p. 2505 - 2512 View in Reaxys

Rx-ID: 1768117 View in Reaxys 54/59 Yield

Conditions & References methylation Iinuma; Iwashima; Matsuura; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 12; (1984); p. 4935 - 4941 View in Reaxys

zinc cyanide

Rx-ID: 5857322 View in Reaxys 55/59

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Yield

Conditions & References T= 50 °C , nachfolgend Hydrolyse des Reaktionsprodukts mit Salzsaeure Gulland; Virden; Journal of the Chemical Society; (1928); p. 1482 View in Reaxys

KMnO4

O HO

sodium carbonate O

Rx-ID: 7059673 View in Reaxys 56/59 Yield

Conditions & References Schnell; Chemische Berichte; vol. 17; (1884); p. 1387 View in Reaxys

–O

Pb4+

O O

Rx-ID: 642868 View in Reaxys 57/59 Yield

Conditions & References Preuss; Menzel; Archiv der Pharmazie (Weinheim, Germany); vol. 291; (1958); p. 377,379-383 View in Reaxys Preuss; Menzel; Archiv der Pharmazie (Weinheim, Germany); vol. 291; (1958); p. 350 View in Reaxys

Rx-ID: 5857319 View in Reaxys 58/59 Yield 96 %

Conditions & References 3 Patent; Wyeth; US2003/204064; (2003); (A1) English View in Reaxys Bose; Chaudhury; Journal of the Indian Chemical Society; vol. 46; (1969); p. 15,19 View in Reaxys Pandit et al.; Journal of Scientific and Industrial Research, Section B: Physical Sciences; vol. 19; (1960); p. 155,157 View in Reaxys Marx et al.; Journal of Heterocyclic Chemistry; vol. 12; (1975); p. 417 View in Reaxys Patent; Upjohn Co.; FR1415670; (1961); ; vol. 64; nb. 5002; (1966) View in Reaxys Millard; Priaulx; Shotton; The Journal of pharmacy and pharmacology; vol. 23; nb. 5; (1971); p. 369 - 373 View in Reaxys Patent; Fuji Photo Film; DE2211436; (1972); ; vol. 78; nb. 3959 View in Reaxys Aratani; Dewar; Journal of the American Chemical Society; vol. 88; (1966); p. 5479,5481 View in Reaxys The following list of compounds exemplifies aromatic and heterocyclic aldehydes useful in carrying out the first step of the processes of this invention leading to the compounds of Formula I. Benzaldehyde, ...

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2-Fluorobenzaldehyde, 4-Isopropylbenzaldehyde, 2,3-Dimethoxybenzaldehyde, 2,4-Dimethoxybenzaldehyde, 2,5-Dimethoxybenzaldehyde, 3,4-Dimethoxybenzaldehyde, 3,5-Dimethoxybenzaldehyde, 2-Butoxy-4-diethylaminobenzaldehyde, ... Patent; The Hilton-Davis Chemical Co.; US4595768; (1986); (A1) English View in Reaxys A few illustrative examples of preferred aldehydes include ... 2,5-dihydroxybenzaldehyde 3,4-dihydroxybenzaldehyde 2,3-dimethoxybenzaldehyde 2,4-dimethoxybenzaldehyde 2,5-dimethoxybenzaldehyde 3,4-dimethoxybenzaldehyde 3,5-dimethoxybenzaldehyde 4,6-dimethoxysalicylaldehyde ... Patent; Ethyl Corporation; US4837327; (1989); (A1) English View in Reaxys 3H

Rx-ID: 7194312 View in Reaxys 59/59 Yield

Conditions & References Aus Phenol (4) mit (CT3O)2-SO2 Malesani,G. et al.; Tetrahedron; vol. 34; (1978); p. 2355 - 2359 View in Reaxys

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