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Process for preparing aryl acetic acid

A technology of aryl acetic acid and amino aryl acetonitrile, applied in nitrile preparation, organic chemistry, etc., can solve the problems of high preparation cost, complex process, high risk, etc., achieve low cost, high reaction yield, and effective recycling Effect

Inactive Publication Date: 2007-02-14
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0030] In order to solve the deficiencies of high preparation cost, complex process, high risk and low yield of arylacetic acid, especially phenylacetic acid, in the prior art, the present invention provides a method with low cost, reasonable process, safe and reliable production, and high reaction yield. The preparation method of high aryl acetic acid

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  • Process for preparing aryl acetic acid
  • Process for preparing aryl acetic acid
  • Process for preparing aryl acetic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0060] Example 1: Synthesis of N-(2,3,4,6-tetrapivaloylglucosyl)-α-aminobenzeneacetonitrile

[0061] At -40°C to -20°C, slowly add dropwise 1 mL of methylene chloride (20 mL) solution containing 3.96 g of trimethylsilyl azide cyanide (37.5 mmol) and CuBr (37.5 mmol) in dichloromethane (20 mL). ) The dichloromethane solution of N-(2,3,4,6-tetrapivaloyl glucosyl) phenylimine. After the dripping is completed, under stirring, the solution is slowly heated to -20°C, and the reaction is at- It was carried out at 20°C and monitored by TLC. After the reaction, the solvent was evaporated, and then the remaining residue was dissolved in 400 mL CH 2 Cl 2 In the organic layer, 2N HCl (100mL), saturated NaHCO 3 (200mL×3) and water (200mL) washing, organic layer with MgSO 4 After drying, the solvent was evaporated to obtain 16.3 g of crude product, with a yield of 86%.

Embodiment 2

[0062] Example 2: Synthesis of N-(2,3,4,6-tetrapivaloylglucosyl)-α-aminobenzeneacetonitrile

[0063] At -20℃~O℃, slowly add 1mL of 30mmol N-( in dichloromethane (20mL) solution containing 3.96g of trimethylsilyl azide cyanide (37.5mmol) and CuBr (37.5mmol) in dichloromethane (20mL). 2,3,4,6-Tetrapivaloyl glucosyl) phenylimine in dichloromethane. After the dripping is completed, under stirring, the solution is slowly warmed to 0°C, and the reaction is carried out at 0°C and monitored by TLC After the reaction, the solvent was evaporated, and then the remaining residue was dissolved in 400mL CH 2 Cl 2 In the organic layer, 2N HCl (100mL), saturated NaHCO 3 (200mL×3) and water (200mL) washing, organic layer with MgSO 4 After drying, the solvent was evaporated to obtain 16.8 g of crude product, with a yield of 89%.

Embodiment 3

[0064] Example 3: Synthesis of N-(2,3,4,6-tetrapivaloylglucosyl)-α-aminobenzeneacetonitrile

[0065] At 0℃~25℃, to a solution of 3.96 grams of trimethylsilyl azide cyanide (37.5mmol) and CuBr (37.5mmol) in dichloromethane (20mL) was slowly added dropwise 1mL containing 30mmol N-(2 ,3,4,6-Tetrapivaloyl glucosyl) aniline in dichloromethane. After dripping, the solution was slowly heated to 25°C under stirring. The reaction was carried out at 25°C and monitored by TLC. After finishing, evaporate the solvent, and then dissolve the remaining residue in 400mL CH 2 Cl 2 In the organic layer, 2N HCl (100mL), saturated NaHCO 3 (200mL×3) and water (200mL) washing, organic layer with MgSO 4 After drying, the solvent was evaporated off after drying, and the solvent was evaporated off after drying to obtain 17.0 g of crude product with a yield of 90%.

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Abstract

The present invention relates to the preparation process of aryl acetic acid as one important intermediate of medicine, pesticide, perfume, etc. The preparation process includes the nucleophilic addition reaction of N-(2, 3, 4, 6-tetrapivaloyl glucityl) aryl amide and trimethyl silicon cyanide under the catalysis of transition metal and Lewis acid inside tetrahydrofuran, acetonitrile, chlorohydrocarbon with 1-3 carbon atoms or alcohol with 3 or 4 carbon atoms to obtain N-(2, 3, 4, 6-tetrapivaloyl glucityl)-alpha-amino aryl acetonitrile, and the hydrolysis of N-(2, 3, 4, 6-tetrapivaloyl glucityl)-alpha-amino aryl acetonitrile in acetic acid solution of hydrogen halide to obtain the aryl acetic acid. The present invention has low cost, high safety, high yield and reuseability of side product.

Description

(1) Technical field [0001] The invention relates to a preparation method of aryl acetic acid, which is an important intermediate of fine chemicals such as medicines, pesticides, spices and the like. (2) Background technology [0002] In the prior art, the chemical synthesis methods related to phenylacetic acid include: [0003] 1. Preparation of target compound by nitrile hydrolysis method: [0004] There are two types of benzylacetonitrile hydrolysis methods: alkaline and acidic hydrolysis, and benzyl cyanide is obtained by condensation of benzyl chloride and sodium cyanide in a certain medium and catalyst. The hydrolysis of benzyl cyanide generally adopts alkaline hydrolysis process, and the reaction is as follows: [0005] <chemistry num="001"> <chem file="200510049166_cml001.xml" / > < / chemistry> [0006] <chemistry num="002"> <chem file="200510049166_cml002.xml" / > < / chemistry> [0007] <chemistry num="003"> <chem file="20051...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C57/32C07C51/08
Inventor 章鹏飞周国斌
Owner HANGZHOU NORMAL UNIVERSITY