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Method for preparing hydroxyl-substituted phenylacetic acid compound

A technology of phenylacetic acid and compounds, which is applied in the field of preparation of hydroxyl-substituted phenylacetic acid compounds, can solve the problems of high equipment requirements, large environmental pollution, and numerous steps, and achieve the effects of small dosage, simple reaction operation, and short reaction time

Inactive Publication Date: 2010-09-15
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the preparation methods of hydroxy-substituted phenylacetic acid compounds mainly include the following: (1) substitution method: using halogenated phenylacetic acid as raw material, copper sulfate pentahydrate or copper powder as catalyst, under high pressure, high temperature and alkaline conditions , carry out substitution reaction to generate hydroxyl-substituted phenylacetic acid; however, this method requires high temperature and high pressure, and requires very high equipment requirements (Fine Petrochemical Progress, 2002, 3: 53-56)
(2) Cyanide method: take hydroxyl-substituted benzaldehyde as a raw material, dehydrate and condense with rhodanine to obtain sulfur-containing derivatives, which are hydrolyzed into corresponding thiocarboxylic acids, react with hydroxylamine to generate hydroxamic acid, and then After acylation and hydrolysis, hydroxyl-substituted phenylacetic acid compounds are obtained; however, this method has many steps, low yield, and great environmental pollution (Journal of Zhengzhou University (Medical Science), 2004, 39 (2): 261-263)

Method used

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  • Method for preparing hydroxyl-substituted phenylacetic acid compound
  • Method for preparing hydroxyl-substituted phenylacetic acid compound
  • Method for preparing hydroxyl-substituted phenylacetic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 3,5-dibromophenylacetic acid (23.44g, 0.08mol), 8-hydroxyquinoline copper (2.82g, 0.008mol) and 30% sodium hydroxide solution (175mL, 1.44mol) were dropped into a stainless steel reaction flask , the temperature of the oil bath was raised to 120° C., stirred and heated to reflux for 6 hours. Stop the reaction, filter (recover the catalyst), acidify the filtrate with hydrochloric acid to PH = 2-3, extract with ethyl acetate, combine the organic layers, concentrate to obtain a red viscous liquid, dissolve with appropriate ethanol, decolorize with 5% activated carbon, Recrystallized from ethanol-chloroform to obtain 12.77 g of white solid 3,5-dihydroxyphenylacetic acid with a yield of about 95%. M.p.123~124℃. 1 HNMR (CD 3 COCD 3 , 400MHz) δ8.208(s, 2H, OH), 6.303~6.297(d, 2H, J=2.4Hz, 2,5-ArH), 6.241~6.230(t, 1H, J=2.4Hz, 4-ArH ), 3.427 (s, 2H, CH 2 ).MS, m / z (%): 168 (M + ).

Embodiment 2

[0027] 3,5-dibromophenylacetic acid (23.44g, 0.08mol), 8-hydroxyquinoline copper (2.82g, 0.008mol) and 30% sodium hydroxide solution (75mL, 0.8mol) were dropped into a stainless steel reaction flask , the temperature of the oil bath was raised to 110° C., stirred and heated to reflux for 6 hours. Stop the reaction, filter (recover the catalyst), acidify the filtrate with hydrochloric acid to PH = 2-3, extract with ethyl acetate, combine the organic layers, concentrate to obtain a red viscous liquid, dissolve with appropriate ethanol, and use 5% activated carbon After decolorization and recrystallization from ethanol-chloroform, 13.03 g of white solid 3,5-dihydroxyphenylacetic acid was obtained, with a yield of about 97%.

Embodiment 3

[0029] 3,5-dibromophenylacetic acid (23.44g, 0.08mol), 8-hydroxyquinoline copper (2.82g, 0.008mol) and 30% sodium hydroxide solution (75mL, 0.8mol) were dropped into a stainless steel reaction flask , the temperature of the oil bath was raised to 80° C., stirred and heated to reflux for 12 hours. Stop the reaction, filter (recover the catalyst), acidify the filtrate with hydrochloric acid to PH = 2-3, extract with ethyl acetate, combine the organic layers, and concentrate to obtain a red viscous liquid, which is dissolved in an appropriate amount of ethyl acetate, 5% Activated carbon was used for decolorization, and ethyl acetate-chloroform recrystallized to obtain 11.15 g of white solid 3,5-dihydroxyphenylacetic acid, with a yield of about 83.0%.

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Abstract

The invention discloses a method for preparing a hydroxyl-substituted phenylacetic acid compound. In the method, under normal pressure, at 80 to 120 DEG C and in a nitrogen protective atmosphere, a halogenated phenylacetic acid compound undergoes a substitution reaction in the presence of 8-oxine-copper(II) and an alkali to form the hydroxyl-substituted phenylacetic acid compound. The method has the advantages of high atomic economy, simple operation, short reaction time, mold reaction conditions, high yield, low cost, less pollution and the like and makes scale preparation realized easily.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of hydroxy-substituted phenylacetic acid compounds. Background technique [0002] Hydroxy-substituted phenylacetic acid compounds are important intermediates in organic synthesis and are widely used in industries such as medicine, pesticides and spices. For example: use 3-hydroxy-4-methoxyphenylacetic acid as a raw material to synthesize the alkaloid dihydrothebainone with analgesic and hypnotic effects; An important raw material of the natural product resveratrol, which has anti-free radical and anti-cancer effects. [0003] At present, the preparation methods of hydroxy-substituted phenylacetic acid compounds mainly include the following: (1) Substitution method: using halogenated phenylacetic acid as raw material, copper sulfate pentahydrate or copper powder as catalyst, under high pressure, high temperature and alkaline conditions , carry out a substitu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/367C07C59/52C07C59/64C07C59/56
Inventor 邹永陈煜魏文肖春芳孙洪宜吕泽良
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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