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Method for synthetising 2-thenoic acetate by thiophene

A technology of thiopheneacetic acid and thiophene, which is applied in the direction of organic chemistry, etc., can solve the problems of difficult separation of intermediate products, low yield of target compounds, unsuitable for industrial production, etc., and achieves obvious economic and environmental benefits, less catalyst consumption, and production cost reduction effect

Inactive Publication Date: 2007-05-02
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has cumbersome reaction steps, difficulties in separating intermediate products, and low yield of target compounds, so it is not suitable for industrial production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 9.25g (0.1mol) of 80% glyoxylic acid, 50ml of formic acid, and 2.46g of anhydrous magnesium sulfate into a 250ml four-necked flask equipped with a mechanical stirrer and a condenser, and stir vigorously at 50°C for 1h. Remove the desiccant by suction filtration, then add 42.0g (0.5mol) thiophene, 1.36g (0.01mol) zinc chloride, and 8.67g (0.07mol) red phosphorus in sequence, and continue to stir at 60°C for 6h, and the temperature of the reaction mixture drops to After room temperature, the unreacted red phosphorus was removed by suction filtration, and the filtrate was distilled under reduced pressure to recover the remaining thiophene and formic acid. The product obtained was crude 2-thiopheneacetic acid. After extraction, washing and recrystallization, 7.55g of 2-thiopheneacetic acid crystals were obtained. Gas chromatography The detected purity is above 98%, and the yield is 53.2% (calculated by glyoxylic acid).

Embodiment 2

[0025] Add 12.33g (0.1mol) of 60% glyoxylic acid and 80ml of glacial acetic acid to a 250ml four-neck flask equipped with a mechanical stirrer and a condenser, slowly add 38.89g of phosphorus pentoxide within 1.5h under stirring conditions, and then Add 16.8g (0.2mol) of thiophene, 0.81g (0.006mol) of stannous oxide, 4.96g (0.04mol) of red phosphorus, and continue to stir at 80°C for 4h. After the temperature of the reaction mixture drops to room temperature, the unreacted red phosphorus, the filtrate is distilled under reduced pressure to recover the remaining thiophene and glacial acetic acid, and the resulting product is the crude product of 2-thiopheneacetic acid. After extraction, washing and recrystallization, 6.80g of 2-thiopheneacetic acid crystals are obtained, and the purity detected by gas chromatography reaches more than 98%. The yield was 47.9% (calculated as glyoxylic acid).

Embodiment 3

[0027] Add 9.25g (0.1mol) of 80% glyoxylic acid, 40ml of propionic acid, and 3.63g of molecular sieve dehydrating agent into a 250ml four-neck flask equipped with a mechanical stirrer and a condenser, and stir vigorously at 40°C for 2 hours. Remove the desiccant by suction filtration, then add 50.4g (0.6mol) of thiophene, 2.72g (0.008mol) of tetrabutyl titanate, and 6.19g (0.05mol) of red phosphorus in sequence, and continue stirring at 50°C for 6h. The temperature of the reaction mixture After cooling down to room temperature, unreacted red phosphorus was removed by suction filtration, and the filtrate was distilled under reduced pressure to recover the remaining thiophene and propionic acid. The resulting product was crude 2-thiopheneacetic acid. After extraction, washing and recrystallization, 7.04g of 2-thiopheneacetic acid crystals were obtained. , the purity detected by gas chromatography reaches more than 98%, and the yield is 49.6% (calculated by glyoxylic acid).

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Abstract

This invention belongs to technique field of fine chemical industry, it relates to a preparation of composing 2-thiophene acetic acid of thiophene, mainly including: after ethanal acid is dewatered, mixed with thiophene and amorphous phosphorus in acid medium, they are reacted by effect of catalytic agent, 2-thiophene acetic acid is obtained. The used ethanal acid is technica grade ethanal acid, in the reactive process the thrown mol share ratio of thiophene and ethanal acid is 1-8:1,when the purity of ethanal acid is lower than 80%, acidity or neutral can be added to raise reaction velocity. Dehydrater addition is adjusted according to purity of ethanal acid to make water content of ethanal acid decrease to lower than 20%, dehydration time is 0.5-2h,dehydration temperature is 20-50DEG C. Thrown mol share ratio of amorphous phosphorus and ethanal acid is 0.2-1.0:1. The used catalytic agent is catalytic agent of un-protonic acid such as stannous oxide, titanium tetrabutoxide, stannic chloride, iron chloride, zinc chloride and so on, Thrown mol share ratio of catalytic agent and ethanal acid is 0.025-0.1:1.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals and relates to a method for synthesizing 2-thiopheneacetic acid from thiophene. Background technique [0002] 2-thiopheneacetic acid is an important intermediate in organic synthesis, widely used in the synthesis of medicines and pesticides, such as the synthesis of cephalosporin drugs, the structural modification of the cephalosporin core 7-aminocephalosporanic acid can improve the drug's antibacterial activity. [0003] There have been some reports on the synthesis of 2-thiopheneacetic acid. In the reported synthesis methods, thiophene is used as a raw material and a multi-step synthesis process is adopted to finally obtain the target product compound. For example, German PatNO.832755 reported that in the presence of various catalysts, thiophene was acetylated with acetyl chloride or acetic anhydride to obtain 2-acetylthiophene, and then reacted with ethanol, sulfur powder, and ammonia ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24
Inventor 张洪林张连红张强李长波蒋林时赵国峥邱峰梁红玉姜虎生凤颀
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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