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ChemicalBook CAS DataBase List 2-CHLORO-4-HYDROXY-BENZOIC ACID METHYL ESTER
104253-44-3

2-CHLORO-4-HYDROXY-BENZOIC ACID METHYL ESTER synthesis

3synthesis methods
Methanol

67-56-1

2-Chloro-4-hydroxybenzoic acid

56363-84-9

2-CHLORO-4-HYDROXY-BENZOIC ACID METHYL ESTER

104253-44-3

General procedure for the synthesis of methyl 2-chloro-4-hydroxybenzoate from methanol and 2-chloro-4-hydroxybenzoic acid: sulfoxide chloride (SOCl2, 1.5 mL) was slowly added to a solution of methanol (10 mL) containing 2-chloro-4-hydroxybenzoic acid (5 g, 0.03 mol). The reaction mixture was gradually heated from room temperature to reflux temperature and reacted under reflux conditions for 12 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to afford the target product methyl 2-chloro-4-hydroxybenzoate (Compound 132A, red solid, 5.4 g, 100% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 10.71 (s, 1H), 7.84-7.71 (m, 1H), 6.91 (d, J = 2.4 Hz, 1H), 6.82 (dd, J = 2.4, 8.7 Hz, 1H), 3.79 (s, 3H).

-

Yield: 100%

Reaction Conditions:

with thionyl chloride for 12 h;Reflux;

Steps:


SOCl2 (1.5 ml) was added to 2-chloro-4-hydroxy-benzoic acid (5 g, 0.03 mmol) in methanol (10 ml). The mixturewas slowly warmed from room temperature to reflux temperature and the reaction solution was refluxed for 12 hoursand concentrated under reduced pressure to give compound 132A (red solid, 5.4 g, the yield was 100%).1H NMR (400MHz, DMSO-d6) δ: 10.71 (s, 1H), 7.84 - 7.71 (m, 1H), 6.91 (d, J=2.4 Hz, 1H), 6.82 (dd, J=2.4, 8.7 Hz, 1H),3.79 (s, 3H).

References:

GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD;LONG, Chaofeng;CHEN, Zhengxia;CHEN, Xiaoxin;ZHANG, Yang;LIU, Zhuowei;LI, Peng;CHEN, Shuhui;LIANG, Guibai;XIE, Cheng;LI, Zhengwei;FU, Zhifei;HU, Guoping;LI, Jian EP3293177, 2018, A1 Location in patent:Paragraph 0332; 0333

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