3,4-Dihydroxybenzaldehyde by Asch

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Reactions (112)

Yield

Substances (10)

Citations (136)

Conditions

References

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With pyridine; aluminium(III) iodide in acetonitrile

T=80°C; 18 h; Hide Experimental Procedure

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Rx-ID: 41582 Find similar reactions

Sang, Dayong; Yao, Ming; Tian, Juan; Chen, Xiaoman; Li, Li; Zhan, Hongju; You, Linhong

Synlett, 2017 , vol. 28, # 1 art. no. ST-2016-W0527-L, p. 138 - 142 Title/Abstract Full Text Show Details

General procedure: To a solution of AlI3 (36.6 mmol, 1.1 equiv) in MeCN (100 mL)was added dropwise a solution of pyridine (12.2 g, 154.2 mmol,4.6 equiv) and eugenol (5.4 g, 33.0 mmol). The mixture wasstirred at 80 °C for 18 h. After cooling to room temperature, themixture was quenched with aq HCl (2 mol/L, 50 mL), and wasextracted with EtOAc (4 × 50 mL). The combined organic phaseswere washed with brine and dried by MgSO4. After evaporationof solvents by a rotary evaporator, the residue was purifiedthrough flash column chromatography to afford 5 as a whitesolid (4.9 g, 99percent). 90%

With 1-butylpyridinium bromide

0.05 h; microwave irradiation;

Chauhan, Shive M. S.; Jain, Nidhi

Journal of Chemical Research, 2004 , # 10 p. 693 - 694 Title/Abstract Full Text View citing articles Show Details

81%

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.

75%

With pyridinium p-toluenesulfonate

0.025 h; microwave irradiation;

Lamba, Mandeep S.; Makrandi, Jagdish K.

Journal of Chemical Research, 2007 , # 10 p. 585 - 586 Title/Abstract Full Text View citing articles Show Details

14%

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

2.5 h; Heating;

Andersson, Sven

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

With aluminum tri-bromide; nitrobenzene

Merz; Fink

Archiv der Pharmazie (Weinheim, Germany), 1956 , vol. 289, p. 347,352, 357 Full Text Show Details

Multi-step reaction with 2 steps 1: pyridine; iodine; dihydrogen peroxide / water 2: dichloromethane; [(2)H6]acetone

UNIVERSITY OF MARYLAND, BALTIMORE; FLETCHER, Steven

Patent: US2014/256817 A1, 2014 ;

With pyridine; aluminum (III) chloride in chloroform

Reflux;

Chen, Hui-Zhen; Chen, You-Bao; Lv, Ya-Ping; Zeng, Fang; Zhang, Juan; Zhou, Yong-Lie; Li, Han-Bing; Chen, Li-Fei; Zhou, Bin-Jie; Gao, Jian-Rong; Xia, Chun-Nian

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 18 p. 4367 - 4371 Title/Abstract Full Text View citing articles Show Details

Title/Abstract Full Text Show Details

View Scheme

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Rx-ID: 625491 Find similar reactions

100%

With boron tribromide in dichloromethane

T=4°C; 1 h;

Sato, Mizuho; Murakami, Kazuma; Uno, Mayumi; Ikubo, Haruko; Nakagawa, Yu; Katayama, Sumie; Akagi, Ken-Ichi; Irie, Kazuhiro

Bioscience, Biotechnology and Biochemistry, 2013 , vol. 77, # 5 p. 1100 - 1103 Title/Abstract Full Text View citing articles Show Details

99.3%

With BBr3*Me2S complex in 1,2-dichloroethane

T=83.5°C; 0.1 h;

Williard, Paul G.; Fryhle, Craig B.

Tetrahedron Letters, 1980 , vol. 21, p. 3731 - 3734 Title/Abstract Full Text View citing articles Show Details

94%

With pyridine; aluminium(III) iodide in acetonitrile

T=80°C; 18 h; Hide Experimental Procedure

Sang, Dayong; Yao, Ming; Tian, Juan; Chen, Xiaoman; Li, Li; Zhan, Hongju; You, Linhong

Synlett, 2017 , vol. 28, # 1 art. no. ST-2016-W0527-L, p. 138 - 142 Title/Abstract Full Text Show Details

With 1-butylpyridinium bromide

0.0333333 h; microwave irradiation;

Chauhan, Shive M. S.; Jain, Nidhi

Journal of Chemical Research, 2004 , # 10 p. 693 - 694 Title/Abstract Full Text View citing articles Show Details

88%

With aluminium(III) iodide; tetra-(nbutyl)ammonium iodide in benzene

1.5 h; Heating;

Andersson, Sven

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

88.9%

With pyridine; aluminum (III) chloride in dichloromethane

T=0 20°C; 24.5 h; Reflux; SolventConcentration; Hide Experimental Procedure

Chongqing Peng Wei Pharmaceutical Co., Ltd.; Yan, Weiwei; Ren, Yanrong; Liu, Zeyan; Han, Gongchao

Patent: CN105566233 A, 2016 ; Location in patent: Paragraph 0015; 0060 ;

2.1:1

the 3L to the three-hole bottle 150g (1eq) vanillin and 1500 ml dichloromethane, stirring, dissolves clear, ice-water bath cooling to 0-10 °C; to a stirring state 334g (2eq) nonaqueous alchlor; temperature in 0-20°C, slowly dropping 392g (5eq) pyridine, after dropping room temperature stirring 30 min; reflux reaction 24h, water bath for cooling to room temperature, dropping 250 ml water and 100 ml concentrated hydrochloric acid mixture finish dripping, cooling to room temperature stirring, until the solid dissolved, should be measured PH 2-3 ; layering after dissolves clear, the water layer is extracted with methylene chloride, combined methylene chloride level ; methylene chloride layer washed with water, water combined; the extraction with ethyl acetate the aqueous layer, combined with the phase; organic phase with saturated salt water washing, drying by anhydrous sodium sulfate, filtered, distilled under reduced pressure to obtain brown solid; in to the residue add 750 ml petroleum ether, room temperature the beating 1h; filtering, the filter cake is washed with petroleum ether washing, drying to obtain 121g solid ELTA, the yield is 88.9percent. 83%

Stage #1: With pyridine; aluminum (III) chloride in 1,2-dichloro-ethane

T=0°C; 2.25 h; Reflux; Stage #2: With hydrogenchloride in water; 1,2-dichloro-ethane

T=0 - 20°C;

Ravindran, Jayaraj; Subbaraju, Gottumukkala V.; Ramani, Modukuri V.; Sung, Bokyung; Aggarwal, Bharat B.

Biochemical Pharmacology, 2010 , vol. 79, # 11 p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

80%

With boron tribromide in dichloromethane

T=-78 - 20°C; 6 h; Inert atmosphere; Hide Experimental Procedure

Luo, Dan; Sharma, Horrick; Yedlapudi, Deepthi; Antonio, Tamara; Reith, Maarten E.A.; Dutta, Aloke K.

Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 21 p. 5088 - 5102 Title/Abstract Full Text Show Details

5.44 3,4-Dihydroxybenzaldehyde (39)

General procedure: BBr3 1M in CH2Cl2 (2.66mL, 2.66mmol) was added to a solution of compound (±)-7a (0.2g, 0.50mmol) in CH2Cl2 (20mL) at −78°C and stirred for 2h. The reaction mixture was allowed to come to room temperature and stirred for another 4h. The reaction was then quenched by MeOH (20mL) at 0° C, and the solvent was concentrated in vacuo. MeOH (20mL) was added to the residue and again evaporated. This process was repeated three times. The residue obtained was purified by column chromatography using 10–15percent MeOH in CH2Cl2 to give pure compound (±)-8a (0.123g, 64percent).

With aluminum tri-bromide; nitrobenzene

With hydrogenchloride

T=180 - 200°C;

Tiemann; Haarmann

Chemische Berichte, 1874 , vol. 7, p. 620 Full Text Show Details

With phosphorus pentachloride

Freudenberg; Heel

Chemische Berichte, 1953 , vol. 86, p. 190,196 Full Text View citing articles Show Details

With pyridine; aluminum (III) chloride in chloroform

Reflux;

Xia, Chun-nian; Li, Hai-bo; liu, Feng; Hu, Wei-xiao

Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 24 p. 6553 - 6557 Title/Abstract Full Text View citing articles Show Details

With aluminum (III) chloride in pyridine

Feng, Jian-Ying; Liu, Zai-Qun

Journal of Agricultural and Food Chemistry, 2009 , vol. 57, # 22 p. 11041 - 11046 Title/Abstract Full Text View citing articles Show Details

With pyridine; aluminum (III) chloride

Pearl; Beyer

Journal of the American Chemical Society, 1953 , vol. 75, p. 2627,2628 Full Text Show Details

Title/Abstract Full Text Show Details

With phosphotungstic acid; sulfuric acid in water

Electrochemical reaction; Reagent/catalyst;

Feng, Jian-Ying; Liu, Zai-Qun

European Journal of Medicinal Chemistry, 2011 , vol. 46, # 4 p. 1198 - 1206 Title/Abstract Full Text View citing articles Show Details

Hossain, Md. Mokarrom; Aldous, Leigh

Electrochemistry Communications, 2016 , vol. 69, p. 32 - 35 Title/Abstract Full Text View citing articles Show Details

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59%

With pyridine; aluminium(III) iodide in acetonitrile

T=80°C; 18 h; Hide Experimental Procedure

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Rx-ID: 44157734 Find similar reactions

Sang, Dayong; Yao, Ming; Tian, Juan; Chen, Xiaoman; Li, Li; Zhan, Hongju; You, Linhong

Synlett, 2017 , vol. 28, # 1 art. no. ST-2016-W0527-L, p. 138 - 142 Title/Abstract Full Text Show Details

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Rx-ID: 36657760 Find similar reactions

44.6 %Chromat.

With copper(II) choride dihydrate in water; ethyl acetate

T=60°C; 5 h; Inert atmosphere;

Bjorsvik, Hans-Rene; Liguori, Lucia; Minisci, Francesco

Organic Process Research and Development, 2000 , vol. 4, # 6 p. 534 - 543 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: mushroom tyrosinase / aq. phosphate buffer / 37 °C / pH 6.8 / |Enzymatic reaction 2: ascorbic acid; perchloric acid / aq. phosphate buffer View Scheme

Ito, Shosuke; Yamanaka, Yuta; Ojika, Makoto; Wakamatsu, Kazumasa

International Journal of Molecular Sciences, 2016 , vol. 17, # 2 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 43051135 Find similar reactions

With perchloric acid; ascorbic acid in aq. phosphate buffer

Rx-ID: 43051142 Find similar reactions

Multi-step reaction with 2 steps 1: mushroom tyrosinase / aq. phosphate buffer / 0.03 h / 37 °C / pH 6.8 / |Enzymatic reaction 2: ascorbic acid; perchloric acid / aq. phosphate buffer View Scheme

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Ito, Shosuke; Yamanaka, Yuta; Ojika, Makoto; Wakamatsu, Kazumasa

International Journal of Molecular Sciences, 2016 , vol. 17, # 2 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 43051149 Find similar reactions

With perchloric acid; ascorbic acid in aq. phosphate buffer

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Ito, Shosuke; Yamanaka, Yuta; Ojika, Makoto; Wakamatsu, Kazumasa

International Journal of Molecular Sciences, 2016 , vol. 17, # 2 Title/Abstract Full Text View citing articles Show Details

Ito, Shosuke; Yamanaka, Yuta; Ojika, Makoto; Wakamatsu, Kazumasa

International Journal of Molecular Sciences, 2016 , vol. 17, # 2 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 43520337 Find similar reactions

81%

With iodine; oxygen; dimethyl sulfoxide

T=80°C; 12 h;

Liang, Yu-Feng; Li, Xinyao; Wang, Xiaoyang; Zou, Miancheng; Tang, Conghui; Liang, Yujie; Song, Song; Jiao, Ning

Journal of the American Chemical Society, 2016 , vol. 138, # 37 p. 12271 - 12277 Title/Abstract Full Text Show Details

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With oxygen; potassium hydoxide in methanol

Sokolová, Romana; Ramešová, Šárka; Kocábová, Jana; Kolivoška, Viliam; Degano, Ilaria; Pitzalis, Emanuela

Monatshefte fur Chemie, 2016 , vol. 147, # 8 p. 1375 - 1383 Title/Abstract Full Text View citing articles Show Details

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98%

With water-d2 in tetrahydrofuran

T=20°C; 18 h; Product distribution / selectivity; Hide Experimental Procedure

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Rx-ID: 28374749 Find similar reactions

CONCERT PHARMACEUTICALS, INC.

Patent: WO2009/35652 A1, 2009 ; Location in patent: Page/Page column 50-52 ; Title/Abstract Full Text Show Details

1; 4:

To a solution of 3,4- dihydroxybenzaldehyde (X) (40 g) in THF (160 mL) was added D2O (160 mL) with stirring. The resulting mixture was stirred overnight at room temperature (rt) under nitrogen. The solvent was removed in vacuo and the residue dried in vacuo at 40 0C overnight to provide XI as a solid (40 g). Analysis by 300 MHz 1H NMR (d6- DMSO) showed an H/D exchange level of approximately 85percent. Example 4. Alternate synthesis of 3,4-Dideuteroxybenzaldehyde (XI). Compound XI was prepared as generally outlined in Scheme 4 above. Details of the conversion are set forth below.Synthesis of 3,4-dideuteroxy benzaldehyde (XI). A 50-L, jacketed reactor equipped with a temperature probe, nitrogenous atmosphere, and reflux condenser was charged with 3,4-dihydroxybenzaldehyde (3.5 kg) and THF (14.0 L). Deuterium oxide (14.0 L) was added and the reaction mixture was stirred for 18 hours (h) at ambient temperature. EtOAc (14 L) was added, and the phases were separated. The aqueous phase was then extracted with EtOAc (14 L). The combined organic layers were concentrated to about 14 L. Toluene was added (14 L) and the suspension was concentrated back down to 14 L. This solvent-swap procedure was repeated two additional times with toluene (14 L each). The solid was collected, and the resulting cake was washed with toluene (10 L). The batch was then dried under high vacuum (40 0C) for 20 h. 3,4-Dideuteroxybenzaldehyde was isolated as a tan solid (3480 g, 98percent yield, greater than 99.9percent AUC by HPLC, 300 MHz 1H NMR indicated a deuteration level of approximately 91percent).

With deuteromethanol; hydrogen chloride

T=20°C; Product distribution / selectivity; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.

Patent: WO2009/35652 A1, 2009 ; Location in patent: Page/Page column 51 ; Title/Abstract Full Text Show Details

To a solution of 3,4- dihydroxybenzaldehyde (X) (25 g) in CH3OD (100 mL) was added DCl (0.4 mL) with stirring. The resulting mixture was stirred overnight at rt and the solvent was removed in vacuo. The residue was re-dissolved in CH3OD (100 mL), DCl (0.4 mL) was added, and the mixture was stirred again overnight at rt. The solvent was removed in vacuo to provide XI as a solid. Analysis by 300 MHz 1H NMR (d6- DMSO) showed an H/D exchange level of approximately 85percent.

With water-d2 in acetonitrile

T=20°C; 96 h; Product distribution / selectivity;

CONCERT PHARMACEUTICALS, INC.

Patent: WO2009/35652 A1, 2009 ; Location in patent: Page/Page column 51 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

To a solution of 3,4- dihydroxybenzaldehyde (X) (10 g) in acetonitrile (200 mL) was added D2O (40 mL) and the resulting mixture was stirred for 4 days at rt. The solvent was removed in vacuo to provide XI as a solid. Analysis by 300 MHz 1H NMR (d6-DMSO) showed an H/D exchange level of approximately 85percent. Hide Details

40 g

With water-d2 in tetrahydrofuran

T=20°C; Inert atmosphere;

Uttamsingh, Vinita; Gallegos, Richard; Liu, Julie F.; Harbeson, Scott L.; Bridson, Gary W.; Cheng, Changfu; Wells, David S.; Graham, Philip B.; Zelle, Robert; Tung, Roger

Journal of Pharmacology and Experimental Therapeutics, 2015 , vol. 354, # 1 p. 43 - 54 Title/Abstract Full Text View citing articles Show Details

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With glycerol-3-Phosphate Dehydrogenase; D-glucose; NADP+; Nocardia PPTase; Segniliparus CAR; 5'-ATP; coenzyme A; magnesium chloride in dimethyl sulfoxide

T=35°C; pH=9; 16 h; Enzymatic reaction; Hide Experimental Procedure

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Rx-ID: 41314262 Find similar reactions

Duan, Yitao; Yao, Peiyuan; Chen, Xi; Liu, Xiangtao; Zhang, Rui; Feng, Jinhui; Wu, Qiaqing; Zhu, Dunming

Journal of Molecular Catalysis B: Enzymatic, 2015 , vol. 115, p. 1 - 7 Title/Abstract Full Text View citing articles Show Details

2.4. Standard reduction procedure

General procedure: The His-CAR (1.5 mg) was incubated with His-PPTase (295 g) in the presence of CoA (1 mM) as a cofactor for 1 h at 28°C in a final volume of 600 L of sodium phosphate buffer (100 mM, pH 7.5) containing 10 mM of MgCl2. The resulting enzyme mixture (holo-CAR, 50 g) was mixed with NADP+ (0.9 mM), GDH (1 U, one unitcorresponds to the amount of enzyme which could reduce 1 molNADP+ to NADPH per minute), glucose (60 mM), MgCl2 (10 mM), substrate (5 or 10 mM, from 1 M stock solution in DMSO), and ATP (15 mM) in Tris–HCl buffer (100 mM, pH 9) with a nal volume of 1 mL. The reaction mixture was incubated at 100 rpm in a rotaryshaker at 35C for 16 h, and extracted with 1 mL of ethyl acetateafter the pH was adjusted to 2–3 with 1 M HCl solution. The organicextracts were dried over anhydrous sodium sulfate and analyzedby gas chromatography (GC) and gas chromatography–mass spec-trometry (GC–MS) to determine the amount of substrate (a) andproducts (aldehyde b, alcohol c) in the mixture. All experimentswere conducted in triplicate.

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87%

With boron tribromide in dichloromethane

T=-78 - 0°C; 6 h; Hide Experimental Procedure

Rx-ID: 6075469 Find similar reactions

WAYNE STATE UNIVERSITY; DUTTA, Aloke, K.

Patent: WO2014/85600 A1, 2014 ; Location in patent: Paragraph 000129 ; Title/Abstract Full Text Show Details

Procedure F'. 4-(5-((2-Amino-4,5,6,7-tetrahydrobenzo[i ]thiazol-6- yl)(propyl)amino)pentyl)benzene-l,2-diol (34).

General procedure: BBr3 1M in DCM (2.66 mL, 2.66 mmol) was added to a solution of compound 32 (0.2 g, 0.532 mmol) in DCM (20 mL) at -78 °C and stirred for 2 h. The reaction mixture was allowed to come to room temperature and stirred for another 4 h. The reaction was then quenched by methanol (20 mL) at 0° C and the solvent was concentrated in vacuo,and MeOH (20 mL) was added to the residue and again evaporated. This process was repeated three times. The residue obtained was purified by column chromatography using 10-15percent methanol in DCM to give pure compound 34(123 mg, 64 percent). 1H NMR (400 MHz, CD3OD) δ ppm 6.64 (d, J = 8.0 Hz, 1H), 6.60 (d, J = 2.4Hz, 1H), 6.47 (dd, J = 8.0, 2.4 Hz, 1H), 3.35-3.40 (m, 1H), 2.752.85 (m, 5H), 2.62-2.71 (m, 2H), 2.55-2.57 (m, 1H), 2.47 (t, J = 7.2 Hz, 2H), 2.09-2.14 (m, 1H), 1.79- 1.89 (m, 1H), 1.57-1.64 (m, 6H), 1.31-1.38 (m, 2H), 0.95 (t, J = 7.6 Hz, 3H). The free base was converted into its corresponding hydrochloride salt. Mp 196-198 °C. Anal. (C2iH34N Cl 02S) C, H, N.

Graesslin,D. et al.

Chemische Berichte, 1967 , vol. 100, p. 3077 - 3083

Full Text View citing articles Show Details

Cunningham,J. et al.

Journal of the Chemical Society, 1963 , p. 2875 - 2883 Full Text View citing articles Show Details

Iskric; Kveder

Croatica Chemica Acta, 1965 , vol. 37, p. 233 Full Text Show Details

Gross et al.

Chemische Berichte, 1963 , vol. 96, p. 308,310 Full Text Show Details

Thomas

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1967 , vol. 348, p. 963,967 Full Text Show Details

Olsson et al.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1978 , vol. 32, p. 249,250,254 Full Text Show Details

Kolodynska; Wieniawski

Acta Poloniae Pharmaceutica, 1967 , vol. 24, p. 261,265,266 Full Text View citing articles Show Details

Monsanto Chem. Co.

Patent: FR1330382 , 1961 ; Chem.Abstr., 1964 , vol. 60, # 2847e Full Text Show Details

Maggioni; Minisci

Chimica e l'Industria (Milan, Italy), 1979 , vol. 61, p. 101,104 Full Text Show Details

Nawata; Umemura

CEER, Chemical Economy and Engineering Review, 1978 , vol. 10, p. 26,27 Full Text Show Details

Crown Zellerbach

Patent: US2975214 , 1961 ; Chem.Abstr., 1961 , vol. 55, # 15422f Full Text Show Details

Forsskahl et al.

Carbohydrate Research, 1976 , vol. 48, p. 13,14-21 Full Text Show Details

Lange

Journal of Organic Chemistry, 1962 , vol. 27, p. 2037 Full Text View citing articles Show Details

Dansette; Azerad

Bulletin de la Societe Chimique de France, 1968 , p. 2492 Full Text Show Details

Prager; Tan

Tetrahedron Letters, 1967 , p. 3661 Full Text View citing articles Show Details

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Kureha Kagaku Kogyo Kabushiki Kaisha

Patent: US4997850 A1, 1991 ; Title/Abstract Full Text Show Details

As the compounds represented by the formula (I), the following compounds can be exemplified: ... 3,4-dioctadecanoyloxybenzylidene dioctadecanoate, 3,4-diacetoxybenzylidene dioctadecanoate, 3,4-dioctadecanoyloxybenzylidene diacetate, 3,4-dibenzoyloxybenzylidene dibenzoate, 3,4-dihydroxybenzaldehyde, 3,4-diacetoxybenzaldehyde, 3,4-dioctadecanoyloxybenzaldehyde, 3,4-dibenzoyloxybenzaldehyde, Hide Details

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A few illustrative examples of preferred aldehydes include ... 3,5-dichlorobenzaldehyde 4-(diethylamino)-benzaldehyde 4-[β-(diethylamino)-ethoxy]-benzaldehyde 2,5-dihydroxybenzaldehyde 3,4-dihydroxybenzaldehyde 2,3-dimethoxybenzaldehyde

Ethyl Corporation

Patent: US4837327 A1, 1989 ; Title/Abstract Full Text Show Details

2,4-dimethoxybenzaldehyde 2,5-dimethoxybenzaldehyde ...

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The Procter and Gamble Company

Patent: US3957424 A1, 1976 ; Title/Abstract Full Text Show Details

Specific examples of formula (C) compounds are: ... 2-chloro-4-hydroxyphenol 2-amino-4-hydroxyphenol 1,3,5-trihydroxybenzene 2,4-dihydroxybenzaldehyde 3,4-dihydroxybenzaldehyde 3,4-dihydroxybenzoic acid 2,4-dihydroxybenzenesulfonic acid 3-ethyl-4-hydroxyphenol ...

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96.1%

in hexadeuterioacetone; dichloromethane

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Rx-ID: 38443225 Find similar reactions

UNIVERSITY OF MARYLAND, BALTIMORE; FLETCHER, Steven

Patent: US2014/256817 A1, 2014 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details

16:3,4-Dihydroxybenzaldehyde (Compound 21)

Example 16 3,4-Dihydroxybenzaldehyde (Compound 21) To a stirred suspension of compound 20 (1.20 g, 4.32 mmol) in CH2Cl2 (40 mL) was added AlCl3 (691 mg, 5.18 mmol) gradually over a period of 5 min. Pyridine (1.53 mL, 19.01 mmol) was then added dropwise to the vigorously stirred mixture. The reaction mixture was refluxed for 20 h, then cooled to 0° C., and acidified to pH ˜1 with 6 N aqueous HCl. TLC analysis revealed the precipitate was mostly the product, which was then dissolved in a minimum volume of acetone. The aqueous layer of the filtrate was separated and extracted with Et2O (3*80 mL). The Et2O extracts were combined with the acetone solution of the precipitate and the resulting mixture was diluted with Et2O (300 mL), and washed with 0.1 N aqueous HCl (3*30 mL). The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and dried under vacuum to afford compound 21 in 96.1percent (1.10 g) yield as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz) δ 10.99 (1H, s, OH), 9.81 (1H, s, CHO), 9.63 (1H, s, OH), 7.24 (1H, d, J=8.4 Hz, Ar), 6.87 (1H, d, J=8.4 Hz, Ar); 13 C-NMR (DMSO-d6, 100 MHz) δ 194.9, 151.4, 146.1, 127.6, 123.6, 115.0, 92.7; MS (ESI) m/z Calcd for C7H5IO3 (M+): 263.9, Found: 264.9 (M+H+).

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98.5%

With BCl *Me S in 1,2-dichloro-ethane

Synthesize Find similar Williard, Paul G.; Fryhle, Craig B.

Rx-ID: 123358 Find similar reactions

T=83.5°C; 29.5 h; other reagent;

Tetrahedron Letters, 1980 , vol. 21, p. 3731 - 3734 Title/Abstract Full Text View citing articles Show Details

84%

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

1.5 h; Heating;

Andersson, Sven

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

68.4%

With titanium tetrachloride in dichloromethane

T=-20 - -10°C; 4 h; Inert atmosphere; Hide Experimental Procedure

Madrid, Alejandro; Espinoza, Luis; Catalan, Karen; Gonzalez, Cesar; Montenegro, Ivan; Mellado, Marco; Werner, Enrique; Cuellar, Mauricio; Villena, Joan

Journal of the Chilean Chemical Society, 2013 , vol. 58, # 3 p. 1814 - 1816 Title/Abstract Full Text View citing articles Show Details

Procedure for the cleavage with TiCl4 solution

The new method of synthesis consisted of a TiCl4 solution (0.9 mL, 8.20mmol) cooled to −20 °C, was slowly added to a solution of piperonal 7 (300 mg,2 mmol) in CH2Cl2 (20 mL) at −10 °C under an atmosphere of N2 with gentlestirring. The reaction was continued for 4 h at −20 °C. After this, the mixturewas taken up in water and then extracted with ethyl acetate (3 × 50 mL). Thewatery layer was discarded and the organic layer was washed to neutrality witha saturated solution of NaHCO3. The organic layer was dried over MgSO4,filtered and evaporated. Then it was absorbed on silica, chromatographedby CC eluting with mixtures of petroleum ether/EtOAc increasing polarity(19.0:1.0→13.0:7.0) to obtain a white solid identified as compound 9 (188.8mg, 68.4 percent); m.p.: 149.8–150.8 °C. IR (cm−1): 3329 (O-H); 2916 (C-H);(C=O); 1616 (C=C); 1430 (-CH2); 809 (-C-H). 1H- NMR: 9.81 (s, 1H, CHO);7.49 (b.s., 1H, OH); 7.44 (b.s., 1H, OH); 7.41 (dd, 1H, J = 8.1, 1.2 Hz, H-5);7.28 (s, 1H, H-3); 6.73 (d, 1H, J = 7.9 Hz, H-6). 13C-NMR: 190.8 (CHO); 151.9(C-1); 145.6 (C-2); 129.2 (C-4); 121.5 (C-5); 115.5 (C-6); 114.6 (C-3). Hide Details

With aluminium trichloride

erst unter Kuehlung, dann bei 130-150grad, neben Vanillin und Isovanillin;

Dreyfus

Patent: DE193958 ;

With Na2S2O5

Fritzsche and Co.

Patent: DE166358 ;

With diluted acid T=185 - 190°C;

With sulphur monochloride

Kochen des Reaktionsprodukts mit Wasser;

Full Text Show Details

Fritzsche and Co.

Patent: DE162822 ; Full Text Show Details

Pauly

Chemische Berichte, 1909 , vol. 42, p. 421 Full Text View citing articles Show Details

Schimmel and Co.

Patent: DE165727 ; Full Text Show Details

Barger

Chemische Berichte, 1909 , vol. 42, p. 764 Full Text View citing articles Show Details

With sulfuryl dichloride

Kochen des Reaktionsprodukts mit Wasser;

Pauly

Chemische Berichte, 1909 , vol. 42, p. 421 Full Text View citing articles Show Details

Schimmel and Co.

Patent: DE165727 ; Full Text Show Details

Barger

Chemische Berichte, 1909 , vol. 42, p. 764 Full Text View citing articles Show Details

With aluminium trichloride; nitrobenzene; toluene

With aluminium trichloride; 1,2-dichloroethane; toluene

Vanillin-Fabr.

Patent: DE591888 , 1932 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 20, p. 532 Full Text Show Details

Givaudan and Cie.

Patent: DE670385 , 1936 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 227 Full Text Show Details

Givaudan-Delawanna Inc.

Patent: US2027148 , 1934 ; Full Text Show Details

With aluminum tri-bromide; nitrobenzene

With aluminum tri-bromide; benzene

Mosettig; Burger

Journal of the American Chemical Society, 1930 , vol. 52, p. 2988,2992 Full Text View citing articles Show Details

Pfeiffer; Ochiai

Journal fuer Praktische Chemie (Leipzig), 1933 , vol. <2> 136, p. 129,131 Full Text Show Details

Pfeiffer; Loewe

Journal fuer Praktische Chemie (Leipzig), 1937 , vol. <2> 147, p. 293,303 Full Text Show Details

With phosphorus pentachloride

(Darst.) und zerlegt das entstandene μ.μDichlor-piperonylidenchlorid mit Wasser erst in der Kaelte zuletzt bei Siedetemperatur;

Buck; Zimmermann

Organic Syntheses, 1938 , vol. 18, p. 75 Full Text Show Details

Murai

Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., vol. 14, p. 153 Chem. Zentralbl., 1925 , vol. 96, # II p. 1746 Full Text Show Details

With thionyl chloride

(Darst.) dann mit Chlor und zersetzt das Reaktionsprodukt mit Wasser;

Hamburger

Patent: DE339945 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 265 Full Text Show Details

With sulphur monochloride

Kochen des Reaktionsproduktes mit Wasser;

Schimmel and Co.

Patent: DE165727 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1277 Full Text Show Details

Schimmel and Co.

Patent: DE223643 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 987 Full Text Show Details

With phosphorus pentachloride; chlorine; toluene

Verseifen der Reaktionsprodukte mit Wasser;

Schmidt,L.

Patent: DE278778 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 175 Full Text Show Details

With sulfuryl dichloride

Kochen des Reaktionsproduktes mit Wasser;

Weisse

Chemische Berichte, 1910 , vol. 43, p. 2605 Full Text View citing articles Show Details

Schimmel and Co.

Patent: DE165727 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1277 Full Text Show Details

With phosphorus; chloroform; chlorine

Verseifen der Reaktionsprodukte mit Wasser;

Schmidt,L.

Patent: DE278778 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 175 Full Text Show Details

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Rx-ID: 606097 Find similar reactions

With iron salt; dihydrogen peroxide

Sommer

Patent: DE155731 ; Full Text Show Details

With water; oxygen; copper; Cu2Cl2

1.) CH3CN; Multistep reaction;

Capdevielle, Patrice; Maumy, Michel

Tetrahedron Letters, 1982 , vol. 23, # 15 p. 1577 - 1580 Title/Abstract Full Text View citing articles Show Details

With mushroom tyrosinase

Enzymatic reaction; Kinetics;

Munoz-Munoz, Jose Luis; Berna, Jose; Garcia-Molina, Maria del Mar; Garcia-Molina, Francisco; Garcia-Ruiz, Pedro Antonio; Varon, Ramon; Rodriguez-Lopez, Jose N.; Garcia-Canovas, Francisco

Biochemical and Biophysical Research Communications, 2012 , vol. 424, # 2 p. 228 - 233 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 33695158 Find similar reactions

49%

Stage #1: [carbonyl-13C]DMF With trichlorophosphate

T=20°C; 0.5 h; Cooling with ice; Stage #2: benzene-1,2-diol T=120°C; 4 h;

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Ueki, Ryosuke; Yamaguchi, Koya; Nonaka, Hiroshi; Sando, Shinsuke

Journal of the American Chemical Society, 2012 , vol. 134, # 30 p. 12398 - 12401 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 34321525 Find similar reactions

A: 1.1 mg B: 1.3 mg C: 2.2 mg D: 0.4 mg E: 2.1 mg F: 1.6 mg G: 0.7 mg H: 23.3 mg I: 2.9 mg J: 0.8 mg K: 32.9 mg L: 1 mg

With hydrogenchloride; water

T=100°C; pH=4.9; 24 h;

Lee, Hyoung Jae; Cho, Jeong-Yong; Moon, Jae-Hak

Fitoterapia, 2012 , vol. 83, # 7 p. 1196 - 1204,9 Title/Abstract Full Text Show Details

Lee, Hyoung Jae; Cho, Jeong-Yong; Moon, Jae-Hak

Fitoterapia, 2012 , vol. 83, # 7 p. 1196 - 1204 Title/Abstract Full Text View citing articles Show Details

M: 0.9 mg

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With iron salt; dihydrogen peroxide

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Rx-ID: 660434 Find similar reactions

Sommer

Patent: DE155731 ; Full Text Show Details

Multi-step reaction with 2 steps 1.1: 1H-imidazole / tetrahydrofuran / 20 °C / Inert atmosphere 1.3: 20 °C 2.1: Pd(OPiv)2; [bis(acetoxy)iodo]benzene / α,α,α-trifluorotoluene / 120 °C / Inert atmosphere 2.2: 20 °C View Scheme

Huang, Chunhui; Ghavtadze, Nugzar; Chattopadhyay, Buddhadeb; Gevorgyan, Vladimir

Journal of the American Chemical Society, 2011 , vol. 133, # 44 p. 17630 - 17633 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With Pd(OPiv)2; [bis(acetoxy)iodo]benzene in α,α,α-trifluorotoluene

T=120°C; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride in tetrahydrofuran

T=20°C; Stage #3: With water in tetrahydrofuran

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Rx-ID: 32049503 Find similar reactions

Huang, Chunhui; Ghavtadze, Nugzar; Chattopadhyay, Buddhadeb; Gevorgyan, Vladimir

Journal of the American Chemical Society, 2011 , vol. 133, # 44 p. 17630 - 17633 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With 1-hydroxy-3H-benz[d] [1,2]iodoxole-1,3-dione in tetrahydrofuran

T=20°C; Darkness; Stage #2: With sodium dithionite; water in tetrahydrofuran

Darkness;

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Pouysegu, Laurent; Sylla, Tahiri; Garnier, Tony; Rojas, Luis B.; Charris, Jaime; Deffieux, Denis; Quideau, Stephane

Tetrahedron, 2010 , vol. 66, # 31 p. 5908 - 5917 Title/Abstract Full Text View citing articles Show Details

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56%

Stage #1: With 1-hydroxy-3H-benz[d] [1,2]iodoxole-1,3-dione in tetrahydrofuran

T=20°C; Darkness; Stage #2: With sodium dithionite; water in tetrahydrofuran

Darkness;

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Rx-ID: 29649441 Find similar reactions

Pouysegu, Laurent; Sylla, Tahiri; Garnier, Tony; Rojas, Luis B.; Charris, Jaime; Deffieux, Denis; Quideau, Stephane

Tetrahedron, 2010 , vol. 66, # 31 p. 5908 - 5917 Title/Abstract Full Text View citing articles Show Details

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With sodium nitrite

pH=2; 0.166667 h; aq. buffer;

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Rx-ID: 31560619 Find similar reactions

Takahama, Umeo; Tanaka, Mariko; Hirota, Sachiko

Free Radical Research, 2010 , vol. 44, # 3 p. 293 - 303 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 31560620 Find similar reactions

With sodium nitrite

pH=2; 1.41667 h; aq. buffer;

Takahama, Umeo; Tanaka, Mariko; Hirota, Sachiko

Free Radical Research, 2010 , vol. 44, # 3 p. 293 - 303 Title/Abstract Full Text View citing articles Show Details

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With hydrogenchloride in acetone

T=0°C; 0.0833333 h;

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Rx-ID: 11261436 Find similar reactions

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

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With hydrogenchloride in acetone

T=0°C; 0.05 h;

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Rx-ID: 11261457 Find similar reactions

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

Synthesize Find similar Rx-ID: 9781751 Find similar reactions

With buffer citrate phosphate; dihydrogen peroxide; benzotriazol-1-ol; Mn(TMePyP) immobilized on clay montmorillonite in 1,4dioxane

T=60°C; pH=6; 4 h; Further byproducts given;

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Crestini, Claudia; Pastorini, Alessandra; Tagliatesta, Pietro

European Journal of Inorganic Chemistry, 2004 , # 22 p. 4477 - 4483 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9872756 Find similar reactions

With 4 A molecular sieve; tin(IV) chloride in dichloromethane

T=-20°C; Friedel-Crafts alkylation; 0.0166667 h;

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Ji, Rong; Schaeffer, Andreas

Journal of Labelled Compounds and Radiopharmaceuticals, 2004 , vol. 47, # 4 p. 209 - 216 Title/Abstract Full Text View citing articles Show Details

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With sodium periodate

pH=3.0; 0.166667 h;

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Rx-ID: 9881902 Find similar reactions

Drag, Marcin; Jezierski, Adam; Kafarski, Pawel

Chemical communications (Cambridge, England), 2004 , # 9 p. 1132 - 1133 Title/Abstract Full Text View citing articles Show Details

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85%

With 1-butylpyridinium bromide

0.0666667 h; microwave irradiation;

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Rx-ID: 9965776 Find similar reactions

Chauhan, Shive M. S.; Jain, Nidhi

Journal of Chemical Research, 2004 , # 10 p. 693 - 694 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: aq. HI / 6 h / Heating 2: NaIO4 / 0.17 h / pH 3.0 View Scheme

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Rx-ID: 13050107 Find similar reactions

Drag, Marcin; Jezierski, Adam; Kafarski, Pawel

Chemical communications (Cambridge, England), 2004 , # 9 p. 1132 - 1133 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1.1: acetyl chloride; acetamide / acetic acid / 4.5 h / 0 - 20 °C 1.2: PCl3 / acetic acid / 2 h / Heating 1.3: aq.HCl / 6 h 2.1: aq. HI / 6 h / Heating 3.1: NaIO4 / 0.17 h / pH 3.0 View Scheme

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Rx-ID: 13051684 Find similar reactions

Drag, Marcin; Jezierski, Adam; Kafarski, Pawel

Chemical communications (Cambridge, England), 2004 , # 9 p. 1132 - 1133 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 23999602 Find similar reactions

66%

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With potassium hydroxide; sulfuric acid in water

Hendel, Wolfram; Heu, Ferdinand; Poechlauer, Peter; Winkler, Berthold

Patent: US2003/45725 A1, 2003 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

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9:Reaction of 3,4-dihydroxyphenylglycine with Isatinsulfonic Acid

EXAMPLE 9 Reaction of 3,4-dihydroxyphenylglycine with Isatinsulfonic Acid A mixture of 18.3 g (100 mmol) of 3,4-dihydroxyphenylglycine and 2.5 g (10 mmol) of sodium isatinsulfonate in 150 ml of water and 6.2 g of conc. sulfuric acid was stirred at 95° C. Oxygen was passed into the mixture for 14 hours. After cooling to RT, the mixture was extracted using 2*100 ml of MTBE, the MTBE phases were combined and washed to neutrality using 200 ml of dilute KOH. After withdrawing the solvent under reduced pressure, 3,4-dihydroxybenzaldehyde was obtained (yield 66percent). A

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Rx-ID: 9059781 Find similar reactions

A: 6% B: 9% C: 10% D: 5%

With acetate buffer; sodium nitrite

T=20°C; pH=4; 4 h; Further byproducts.;

Napolitano, Alessandra; D'Ischia, Marco

Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 803 - 810 Title/Abstract Full Text View citing articles Show Details

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Find similar Rx-ID: 9131993 Find similar reactions

With oxygen; acetic acid; bismuth in water; dimethyl sulfoxide

T=125°C; P=760.051 Torr; 1 h;

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Favier, Isabel; Giulieri, Francoise; Dunach, Elisabet; Hebrault, Dominique; Desmurs, Jean-Roger

European Journal of Organic Chemistry, 2002 , # 12 p. 1984 - 1988 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9199546 Find similar reactions

A: 58% B: 20%

With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol

0.25 h; Heating;

Chakraborti, Asit K.; Sharma, Lalima; Nayak, Mrinal K.

Journal of Organic Chemistry, 2002 , vol. 67, # 18 p. 6406 - 6414 Title/Abstract Full Text View citing articles Show Details

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94%

With sulfuric acid; water; silica gel in toluene

T=60 - 70°C; 1.25 h;

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Rx-ID: 9348974 Find similar reactions

Mirjalili, BiBi Fathemeh; Zolfigol, Mohamad Ali; Bamoniri, Abdolhamid

Molecules, 2002 , vol. 7, # 10 p. 751 - 755 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 8861546

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in acetonitrile

T=20°C; 2.5 h;

Ariza; Pineda; Vilarrasa; Shipps Jr.; Ma; Dai

Organic letters, 2001 , vol. 3, # 9 p. 1399 - 1401 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 8861552 Find similar reactions

in acetonitrile

T=20°C; 3 h;

Ariza; Pineda; Vilarrasa; Shipps Jr.; Ma; Dai

Organic letters, 2001 , vol. 3, # 9 p. 1399 - 1401 Title/Abstract Full Text View citing articles Show Details

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With oxygen; iron powder in phosphate buffer

Oxidation; pH=7.0; 20 h; Kinetics;

Napolitano, Alessandra; Pezzella, Alessandro; Prota, Giuseppe

Tetrahedron Letters, 1999 , vol. 40, # 14 p. 2833 - 2836 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5200134 Find similar reactions

With oxygen; iron powder in phosphate buffer

Oxidation; rearrangement; pH=7.0;

Napolitano, Alessandra; Pezzella, Alessandro; Prota, Giuseppe

Tetrahedron Letters, 1999 , vol. 40, # 14 p. 2833 - 2836 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 5218697 Find similar reactions

With oxygen; iron powder in phosphate buffer

Oxidation; rearrangement; pH=7.0;

Napolitano, Alessandra; Pezzella, Alessandro; Prota, Giuseppe

Tetrahedron Letters, 1999 , vol. 40, # 14 p. 2833 - 2836 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 4692448 Find similar reactions

30%

With trichlorophosphate in benzene

a) RT, overnight, b) from 65 deg C to 70 deg C, 2 h;

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Li, Shu Wen; Spaziano, Vincent T.; Elliott, William H.; Burke, William J.

Bioorganic Chemistry, 1996 , vol. 24, # 2 p. 169 - 177 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3799276 Find similar reactions

With singlet oxygen in water

T=20°C; Rate constant;

Jovanovic, Slobodan V.; Steenken, Steen; Tosic, Mihajlo; Marjanovic, Budimir; Simic, Michael G.

Journal of the American Chemical Society, 1994 , vol. 116, # 11 p. 4846 - 4851 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2720059 Find similar reactions

With potassium hydroxide; βcyclodextrin in water

T=60°C; Yield given;

Divakar, S.; Maheswaran, M. M.; Narayan, M. S.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992 , vol. 31, # 8 p. 543 - 546 Title/Abstract Full Text Show Details

With potassium hydroxide; βcyclodextrin in water

T=60°C;

Divakar, S.; Maheswaran, M. M.; Narayan, M. S.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992 , vol. 31, # 8 p. 543 - 546 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 2748599 Find similar reactions

With lithium chloride in N,N-dimethylformamide

22 h; Heating; Yield given. Yields of byproduct given;

Bernard, Angela M.; Ghiani, M. Rossella; Piras, Pier Paolo; Rivoldini, Antonio

Synthesis, 1989 , # 4 p. 287 - 289 Title/Abstract Full Text Show Details

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27%

With silver; sodium hydrogencarbonate; sodium iodide; zinc in ethylene glycol dimethyl ether; dimethyl sulfoxide

T=80°C; 6 h;

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Rx-ID: 2040246 Find similar reactions

Chung, Chi Kong; Ho, Mei Sing; Lun, Kue Sun; Wong, Man On; Wong, Henry N. C.; Tam, Shang Wai

Synthetic Communications, 1988 , vol. 18, # 5 p. 507 - 510 Title/Abstract Full Text Show Details

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79.9%

With potassium hydroxide; lithium perchlorate in water; acetonitrile

T=0°C; cathodic reduction at Pt electrode;

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Rx-ID: 2083101 Find similar reactions

Yanilkin, V. V.; Dudenko, L. Yu.; Babkin, V. A.; Ivanova, S. Z.; Medvedev, V. A.

J. Gen. Chem. USSR (Engl. Transl.), 1986 , vol. 56, # 5 p. 1139 - 1145,1001 - 1006 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 3123421 Find similar reactions

B: 85%

With tetrafluoroboric acid; [Fe(bipy)3]2+ in water; acetonitrile

0.0833333 h; Ambient temperature;

Murase, Masayuki; Kotani, Eiichi; Tobinaga, Seisho

Chemical and Pharmaceutical Bulletin, 1986 , vol. 34, # 9 p. 3595 - 3598 Title/Abstract Full Text Show Details

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Rx-ID: 18560707

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Multi-step reaction with 3 steps 1: 13.7 percent / 0.1 N KOH, 0.05 N LiClO4 / acetonitrile; H2O / 0 °C / anodic oxidation at Pt electrode 2: 87.6 percent / 0.1 N KOH, 0.05 N LiClO4 / acetonitrile; H2O / 0 °C / anodic oxidation at Pt electrode 3: 79.9 percent / 0.1 N KOH, 0.05 N LiClO4 / acetonitrile; H2O / 0 °C / cathodic reduction at Pt electrode View Scheme

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Yanilkin, V. V.; Dudenko, L. Yu.; Babkin, V. A.; Ivanova, S. Z.; Medvedev, V. A.

J. Gen. Chem. USSR (Engl. Transl.), 1986 , vol. 56, # 5 p. 1139 - 1145,1001 - 1006 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 87.6 percent / 0.1 N KOH, 0.05 N LiClO4 / acetonitrile; H2O / 0 °C / anodic oxidation at Pt electrode 2: 79.9 percent / 0.1 N KOH, 0.05 N LiClO4 / acetonitrile; H2O / 0 °C / cathodic reduction at Pt electrode View Scheme

Rx-ID: 18572812 Find similar reactions

Yanilkin, V. V.; Dudenko, L. Yu.; Babkin, V. A.; Ivanova, S. Z.; Medvedev, V. A.

J. Gen. Chem. USSR (Engl. Transl.), 1986 , vol. 56, # 5 p. 1139 - 1145,1001 - 1006 Title/Abstract Full Text Show Details

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Hide Experimental Procedure

Rx-ID: 25136407 Find similar reactions

Kureha Kagaku Kogyo Kabushiki Kaisha

Patent: US4464396 A1, 1984 ; Title/Abstract Full Text Show Details

2:Preparation of trans-4-[N-(3',4'-dihydroxybenzyl)aminomethyl]cyclohexane-1-carboxylic acid

EXAMPLE 2 Preparation of trans-4-[N-(3',4'-dihydroxybenzyl)aminomethyl]cyclohexane-1-carboxylic acid 5.0 g (18.0 mmol) of trans-4-[N-(3',4'-dihydroxybenzylidene)aminomethyl]cyclohexane-1-carboxylic acid obtained by condensation of 3,4-dihydroxybenzaldehyde with trans-4-aminomethylcyclohexane-1-carboxylic acid was dissolved in 50 ml of methanol. Into the resulting solution, 0.963 mg (25.4 mmol) of sodium borohydride was added while stirring at room temperature, and after further adding 30 ml of methanol, the mixture was reacted for 10 minutes at room temperature. After the reaction was over, a minute amount of insoluble matters were removed by filtration followed by neutralizing the reaction mixture with hydrochloric acid, the solvent was evaporated off from the reaction mixture under a reduced pressure to obtain 4.03 g of a crude product. The crude product was dissolved in a mixture of 8 ml of distilled water and 21 ml of concentrated hydrochloric acid at 60° to 65° C.

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With hydrogen bromide

15 h; Ambient temperature;

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Rx-ID: 3697476 Find similar reactions

Corsano; Proietti; Castagnino; Strappaghetti

Farmaco, Edizione Scientifica, 1983 , vol. 38, # 4 p. 265 - 273 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 1) AlCl3, 2) 10percent HCl / 1) benzene, temp ,40 deg C, 2) benzene, 1 h, 50 deg C 2: 48percent HBr / 15 h / Ambient temperature View Scheme

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Rx-ID: 18571641 Find similar reactions

Corsano; Proietti; Castagnino; Strappaghetti

Farmaco, Edizione Scientifica, 1983 , vol. 38, # 4 p. 265 - 273 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 78 percent / NaOEt / dimethylformamide / 0.5 h / Ambient temperature 2: 1) AlCl3, 2) 10percent HCl / 1) benzene, temp ,40 deg C, 2) benzene, 1 h, 50 deg C 3: 48percent HBr / 15 h / Ambient temperature View Scheme

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Rx-ID: 18572441 Find similar reactions

Corsano; Proietti; Castagnino; Strappaghetti

Farmaco, Edizione Scientifica, 1983 , vol. 38, # 4 p. 265 - 273 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 1888260 Find similar reactions

A: 0.04% B: 0.03% C: 0.01% D: 0.15% E: 0.01% F: 0.03%

With acetate buffer

45 h; Heating; Product distribution;

Theander, Olof; Westerlund, Eric

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1980 , vol. 34, # 10 p. 701 - 706 Title/Abstract Full Text Show Details

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62.4%

Hide Experimental Procedure

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Rx-ID: 25336683 Find similar reactions

Ube Industries, Ltd.

Patent: US4165341 A1, 1979 ; Title/Abstract Full Text Show Details

C.1:COMPARATIVE EXAMPLE 1

The conversion of catechol was 62.4percent, the yield of protocatechualdehyde was 3.06 g and the selectivity was 71.1percent.

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Dihydroxybenzaldehyd, D2O, Triaethylamin;

Rx-ID: 7595498 Find similar reactions

Roughley; Whiting

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973 , p. 2379,2388 Full Text Show Details

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Dihydroxybenzaldehyd, Tritium-haltiges H2O/Triaethylamin (Aktivitaet: 4.4Ci/cm3);

Rx-ID: 7595508 Find similar reactions

Roughley; Whiting

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973 , p. 2379,2388 Full Text Show Details

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Vanillin(14C-Ring), BBr3;

Rx-ID: 7204884 Find similar reactions

Haider

Journal of Labelled Compounds, 1966 , vol. 2, p. 174,180 Full Text Show Details

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2,6-Ditritio-isovanillin, durch Demethylierung;

Rx-ID: 7655290 Find similar reactions

Kirby,G.W.; Ogunkoya,L.

Journal of the Chemical Society, 1965 , p. 6914 - 6922 Full Text View citing articles Show Details

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Rx-ID: 300989 Find similar reactions

With 4-nitroso-N,N-di-methylaniline

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Eliseewa; Dewizkaja

Trudy Inst.sint.nat.dusist.VescestvChem.Abstr., 1958 , # 4 p. 31,33 Trudy Inst.sint.nat.dusist.VescestvChem.Abstr., 1960 , p. 1391 Full Text Show Details

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With pyridine hydrochloride

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Rx-ID: 384586 Find similar reactions

Beke; Szantay

Acta Chimica Academiae Scientiarum Hungaricae, 1957 , vol. 12, p. 275,279 Full Text Show Details

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Rx-ID: 77151 Find similar reactions

auch unter Zusatz von Dibenzoylperoxid;

Yamaguchi

Nippon Kagaku Zasshi, 1956 , vol. 77, p. 513 Chem.Abstr., 1958 , p. 9014 Full Text View citing articles Show Details

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Rx-ID: 266732 Find similar reactions

T=160°C;

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

T=190°C;

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

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Rx-ID: 331770 Find similar reactions

With sodium hydroxide

T=150 - 200°C;

Baum

Patent: DE82078 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 134 Full Text Show Details

With sodium hydroxide; water; copper

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

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With sodium hydroxide; water; copper(I) bromide

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

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With sodium hydroxide; copper

unter Druck;

Boehringer and Soehne

Patent: DE269544 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 190 Full Text Show Details

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With sodium hydroxide; copper salts

unter Druck;

Boehringer and Soehne

Patent: DE269544 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 190 Full Text Show Details

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Rx-ID: 7449988 Find similar reactions

T=160°C;

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

T=190°C;

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

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Rx-ID: 7449989 Find similar reactions

T=190°C;

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

T=160°C;

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

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Rx-ID: 7449990 Find similar reactions

T=160°C;

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

T=190°C;

Shinra; Shinra

Kogyo Kagaku Zasshi, 1944 , vol. 47, p. 168,170 Chem.Abstr., 1949 , p. 1974 Full Text Show Details

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Rx-ID: 619580 Find similar reactions

With hydrogenchloride; castiron; water; sodium o-nitrobenzenesulfonate

man filtriert vom Eisenschlamm ab, saettigt dann mit NaCl und aethert den Protocatechualdehyd aus;

Geigy and Co.

Patent: DE105798 ;

With hydrogenchloride; aluminium; mnitrobenzene sulfonic acid sodium salt

Schorygin et al.

Zhurnal Obshchei Khimii, 1938 , vol. 8, p. 975,978 Chem. Zentralbl., 1939 , vol. 110, # I p. 2178 Full Text View citing articles Show Details

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Full Text Show Details

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With methanol; mineral acid

With sodium hydrogensulfite

und anschliessendes Erhitzen mit wss.H2SO4;

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Rx-ID: 293922 Find similar reactions

Riedel-de Haen

Patent: DE563127 , 1929 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 761 Full Text Show Details

Kimura

Kogyo Kagaku Zasshi, 1937 , vol. 40, p. 600,603 J. Soc. chem. Ind. Japan Spl., 1937 , vol. 40, p. 277 Full Text Show Details

Stockelbach

Patent: US1792716 , 1927 ; Full Text Show Details

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With potassium hydroxide; nitrobenzene

T=120 - 130°C;

Rx-ID: 6075473 Find similar reactions

Kimura

Kogyo Kagaku Zasshi, 1937 , vol. 40, p. 600,603 J. Soc. chem. Ind. Japan Spl., 1937 , vol. 40, p. 277 Full Text Show Details

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Multi-step reaction with 2 steps

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Rx-ID: 22096263 Find similar reactions

1: nitrobenzene; concentrated aqueous alkaline solution / 120 - 130 °C 2: aqueous NaHSO3 / und anschliessendes Erhitzen mit wss.H2SO4

View Scheme

Kogyo Kagaku Zasshi, 1937 , vol. 40, p. 600,603 J. Soc. chem. Ind. Japan Spl., 1937 , vol. 40, p. 277 Full Text Show Details

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With sodium hydroxide; dihydrogen peroxide

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Rx-ID: 305109 Find similar reactions

Hoffmann-La Roche

Patent: DE530650 , 1930 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 566 Full Text Show Details

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Rx-ID: 7448474 Find similar reactions

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Hoffmann-La Roche A.G.

Patent: DE530650 , 1930 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 566 Full Text Show Details

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Rx-ID: 619887 Find similar reactions

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With trichlorophosphate

T=20°C; und Kochen des Reaktionsprodukts mit 3prozentiger Natronlauge;

Froeschl; Bomberg

Monatshefte fuer Chemie, 1927 , vol. 48, p. 573 Full Text Show Details

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Rx-ID: 6075475 Find similar reactions

nachfolgend Kochen mit Natronlauge;

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Froeschl; Bomberg

Monatshefte fuer Chemie, 1927 , vol. 48, p. 573 Full Text Show Details

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With potassium hydroxide; acetone

T=5°C;

Rx-ID: 7448475 Find similar reactions

Pacsu; v. Vargha

Chemische Berichte, 1926 , vol. 59, p. 2823 Full Text Show Details

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Rx-ID: 7457442 Find similar reactions

Hydrolysis;

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Pacsu; v.Vargha

Chemische Berichte, 1926 , vol. 59, p. 2819

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Full Text Show Details

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Rx-ID: 619643 Find similar reactions

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Reihlen; Illig; Wittig

Chemische Berichte, 1925 , vol. 58, p. 18 Full Text Show Details

Reimer; Tiemann

Chemische Berichte, 1876 , vol. 9, p. 1269 Full Text Show Details

Tiemann; Koppe

Chemische Berichte, 1881 , vol. 14, p. 2021 Full Text Show Details

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Rx-ID: 619645 Find similar reactions

With sodium hydroxide

With potassium hydroxide

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Reihlen; Illig; Wittig

Chemische Berichte, 1925 , vol. 58, p. 18 Full Text Show Details

Reimer; Tiemann

Chemische Berichte, 1876 , vol. 9, p. 1269 Full Text Show Details

Tiemann; Koppe

Chemische Berichte, 1881 , vol. 14, p. 2021 Full Text Show Details

Reihlen; Illig; Wittig

Chemische Berichte, 1925 , vol. 58, p. 18 Full Text Show Details

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With potassium hydroxide

aufeinanderfolgenden Behandeln des Reaktionsprodukts in Aethylacetat mit Ozon,mit wss.Na2S2O4 und mit wss.NaHSO3 und Versetzen der wss.Reaktionsloesung mit Schwefelsaeure;

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Rx-ID: 809048 Find similar reactions

Schimmel and Co.

Patent: DE513678 , 1925 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 2599 Full Text Show Details

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Rx-ID: 5700964 Find similar reactions

T=150 - 200°C;

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Pascal

Bulletin de la Societe Chimique de France, 1925 , vol. <4> 37, p. 1043 Full Text View citing articles Show Details

Spaeth; Lang

Chemische Berichte, 1921 , vol. 54, p. 3074 Full Text Show Details

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Rx-ID: 6075477 Find similar reactions

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Reihlen; Illig; Wittig

Chemische Berichte, 1925 , vol. 58, p. 18 Full Text Show Details

Reimer; Tiemann

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Chemische Berichte, 1876 , vol. 9, p. 1269 Full Text Show Details

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Rx-ID: 26605083 Find similar reactions

With hydrogenchloride in hydrogenchloride

addn. of excess of concd. HCl to concd. hot aq. soln.;

Reihlen, H.; Sapper, A.

Zeitschrift fuer Anorganische und Allgemeine Chemie, 1922 , vol. 124, p. 275 - 288 Full Text Show Details

With HCl in hydrogenchloride

Gmelin Handbook: Ni: MVol.C2, 1, page 497 - 504 Full Text Show Details

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With water

With diluted acids

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Rx-ID: 165691 Find similar reactions

Delange

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1907 , vol. 144, p. 1279 Bulletin de la Societe Chimique de France, 1908 , vol. <4> 3, p. 506 Full Text View citing articles Show Details

Fittig; Remsen

Justus Liebigs Annalen der Chemie, 1871 , vol. 159, p. 145 Full Text View citing articles Show Details

Wegscheider

Monatshefte fuer Chemie, 1893 , vol. 14, p. 383 Anm. 1 Full Text Show Details

Delange

Fittig; Remsen

Justus Liebigs Annalen der Chemie, 1871 , vol. 159, p. 145 Full Text View citing articles Show Details

Wegscheider

Monatshefte fuer Chemie, 1893 , vol. 14, p. 383 Anm. 1 Full Text Show Details

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Rx-ID: 5700966 Find similar reactions

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Pauly

Chemische Berichte, 1907 , vol. 40, p. 3097,3099 Chem. Zentralbl., 1908 , vol. 79, # I p. 685 Full Text View citing articles Show Details

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Rx-ID: 5700968 Find similar reactions

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Delange

Fittig; Remsen

Justus Liebigs Annalen der Chemie, 1871 , vol. 159, p. 145 Full Text View citing articles Show Details

Schimmel and Co.

Patent: DE165727 ;

Full Text Show Details

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Rx-ID: 5700969 Find similar reactions

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Rx-ID: 7919942 Find similar reactions

T=60°C;

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Abel; Taveau

Chem. Zentralbl., 1906 , vol. 77, # I p. 765 Full Text Show Details

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Rx-ID: 7919943 Find similar reactions

T=160 - 170°C;

Wegscheider

Monatshefte fuer Chemie, 1882 , vol. 3, p. 791 Monatshefte fuer Chemie, 1893 , vol. 14, p. 383 Full Text Show Details

Wegscheider

Monatshefte fuer Chemie, 1893 , vol. 14, p. 383 Anm. 1 Full Text Show Details

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Rx-ID: 384587 Find similar reactions

With hydrogenchloride; water

T=170°C;

Wegscheider

Monatshefte fuer Chemie, 1882 , vol. 3, p. 791 Monatshefte fuer Chemie, 1893 , vol. 14, p. 383 Full Text Show Details

With hydrogenchloride; water

T=160 - 170°C;

Wegscheider

Monatshefte fuer Chemie, 1882 , vol. 3, p. 791 Monatshefte fuer Chemie, 1893 , vol. 14, p. 383 Full Text Show Details

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Multi-step reaction with 2 steps 1: potassium hydroxide / durch Schmelzen 2: NaOH-solution View Scheme

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Rx-ID: 22148619 Find similar reactions

Tiemann; Koppe

Chemische Berichte, 1881 , vol. 14, p. 2021 Full Text Show Details

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Rx-ID: 6075480 Find similar reactions

T=180 - 200°C;

Tiemann; Haarmann

Chemische Berichte, 1874 , vol. 7, p. 620 Full Text Show Details

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Multi-step reaction with 2 steps 1: potassium dichromate; sulfuric acid 2: diluted hydrochloric acid / 180 - 200 °C View Scheme

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Rx-ID: 22039760 Find similar reactions

Tiemann; Haarmann

Chemische Berichte, 1874 , vol. 7, p. 620 Full Text Show Details

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With hydrogenchloride

T=200°C;

Rx-ID: 6075470 Find similar reactions

Fittig; Remsen

Justus Liebigs Annalen der Chemie, 1873 , vol. 168, p. 94 Full Text View citing articles Show Details

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Rx-ID: 56321 Find similar reactions

Chem.Fabr.Schering

Patent: DE82747 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 1286 Full Text Show Details

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Rx-ID: 331765 Find similar reactions

T=150 - 200°C; unter Druck;

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Baum

Patent: DE82078 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 134 Full Text Show Details

Boehringer and Soehne

Patent: DE269544 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 190 Full Text Show Details

Baum

Patent: DE82078 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 134 Full Text Show Details

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Rx-ID: 364318 Find similar reactions

T=150 - 180°C; unter Druck;

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Baum

Patent: DE82078 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 134 Full Text Show Details

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Dreyfus

Patent: DE193958 ; Full Text Show Details

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