Preparation method for aryl acetic acid derivative

A technology of derivatives and aromatic groups, which is applied in the field of preparation of aromatic acetic acid derivatives, can solve problems such as shortage of raw material sources, troublesome post-processing, and large environmental pollution, and achieves suitable for large-scale industrial production, mild reaction conditions, The effect of little environmental pollution

Inactive Publication Date: 2011-05-25
GUILIN NORMAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These existing methods have high production costs (reflected as high requirements for production equipment, and the price of raw materials or catalysts is relatively expensive), raw material sources are in short supply, the reaction time is long, the environment is polluted, post-processing is troublesome, and the purification of impurities in the product is difficult. Ultimately affect product quality; Moreover, these preparation methods are only applicable to the preparation of a compound, and the scope of application is narrow, resulting in a lot of aryl acetic acid being in short supply on the market, and the price is very expensive

Method used

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  • Preparation method for aryl acetic acid derivative
  • Preparation method for aryl acetic acid derivative
  • Preparation method for aryl acetic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the preparation of phenylacetic acid

[0020] Weigh 10.6kg of benzaldehyde, 11.7kg of N-acetylglycine, 8.0kg of sodium acetate and 6.0kg of acetic anhydride in an ultrasonic reactor, react for 1 hour at a temperature of 80°C and a working frequency of 40kHz, and filter after cooling , add 7.1kg of 20% sodium hydroxide aqueous solution, mix evenly, pour 17.0kg of 30% hydrogen peroxide, react for 1h at a temperature of 20°C and a working frequency of 40kHz, filter to obtain crude phenylacetic acid, use petroleum After ether recrystallization, 8.9 kg of flaky phenylacetic acid crystals were obtained, with a content of 99.5%, a yield of 65%, and a melting point of 75-77°C. The nuclear magnetic resonance data of gained product is: 1 H NMR (500MHz, CDCl 3 ): δ3.52 (s, 2H, -CH2-), 7.14 to 7.19 (m, 5H, H-Ph), 11.17 (s, IH, COOH).

[0021] The reaction formula is as follows:

[0022]

Embodiment 2

[0023] Embodiment 2: the preparation of phenylacetic acid

[0024] Weigh 3.2kg of benzaldehyde, 3.5kg of N-acetylglycine, 2.4kg of sodium acetate and 1.8kg of acetic anhydride in a round-bottomed flask, reflux at 100°C for 2 hours, filter after cooling, and add 20% hydroxide 3.2 kg of sodium aqueous solution, after mixing evenly, pour 5.1 kg of 30% hydrogen peroxide, stir and react at 40° C. for 2.5 h, filter to obtain crude phenylacetic acid, recrystallize with petroleum ether to obtain 0.8 kg of flaky phenylacetic acid crystals, The content is 99.3%, the yield is 48%, and the melting point is 75-77°C. The nuclear magnetic resonance data of gained product is: 1 H NMR (500MHz, CDCl 3 ): δ3.52 (s, 2H, -CH2-), 7.14 to 7.19 (m, 5H, H-Ph), 11.17 (s, IH, COOH).

[0025] The reaction formula is as follows:

[0026]

Embodiment 3

[0027] Embodiment 3: Preparation of p-nitrophenylacetic acid crystals

[0028] Weigh 13.6kg of p-nitrobenzaldehyde, 10.5kg of N-acetylglycine, 7.0kg of sodium acetate and 5.4kg of acetic anhydride and place them in an ultrasonic reactor, and react for 1 hour at a temperature of 70°C and a working frequency of 55kHz. After cooling, filter, add 7.1kg of 5% sodium hydroxide aqueous solution, mix evenly, pour 15.3kg of 30% hydrogen peroxide, react for 1h at a temperature of 25°C and a working frequency of 55kHz, and filter to obtain p-nitro The crude product of phenylacetic acid was recrystallized with hot water to obtain 10.2 kg of p-nitrophenylacetic acid crystals, with a content of 99.3%, a yield of 68%, and a melting point of 153-154°C. The nuclear magnetic resonance data of gained product is: 1 H NMR (500MHz, CDCl 3 ): δ3.38(s, 2H, -CH2-), 7.34~7.35(d, J=8.2Hz, 2H, H-Ph), 7.43~7.45(d, J=7.5Hz, 2H, H-Ph) , 11.11 (s, IH, COOH).

[0029] The reaction formula is as follows: ...

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Abstract

The invention discloses a preparation method for an aryl acetic acid derivative. The preparation method comprises the following specific steps of: (1) adding sodium acetate, acetic anhydride and a cyclization agent into aryl methanal or alkyl original aliphatic aldehyde having more than four carbon atoms, and performing cyclization reaction to obtain an aryl oxazolone derivative, wherein the cyclization agent is N-acyl-glycine or an analogue thereof; and (2) uniformly mixing the aryl oxazolone derivative and aqueous alkali, adding an oxidizing agent and performing oxidization reaction to obtain the corresponding aryl acetic acid derivative, wherein the alkali is sodium hydroxide solution or potassium hydroxide, and the oxidizing agent is peroxy acid. Compared with the prior art, the method is mild in reaction condition, short in reaction steps, short in preparation cycle, low in cost, simple in posttreatment and low in environmental pollution, and is applicable for preparation of the aryl acetic acid derivative; by the method, the raw materials are readily available; moreover, the product prepared by the method is high in purity and stable in quality, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of aromatic acetic acid derivatives. Background technique [0002] Arylacetic acid derivatives are an important class of chemical and pharmaceutical intermediates, and are widely used in the synthesis of medicines. For example, phenylacetic acid is used in the production of penicillin, dimethazole and other drugs, 2-methyl-3-nitrophenylacetic acid is an intermediate of Parkinson’s disease treatment drug ropinirole, 2,4,5-trifluorobenzene Acetic acid is an important intermediate for preparing new diabetes drugs, and 3-ethoxy-4-ethoxycarbonylphenylacetic acid is an intermediate for synthesizing repaglinide, a drug for treating type 2 diabetes. [0003] At present, the preparation of aryl acetic acid derivatives is mainly based on corresponding halogen compounds, nitrates, etc. as raw materials, and the corresponding aryl acetic acid comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/285C07C57/32C07C201/12C07C205/56C07C59/64C07C57/58C07C57/50C07C59/52C07C53/126
Inventor 张业义祥辉刘贤贤王凯
Owner GUILIN NORMAL COLLEGE
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