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Green preparation technology of 2-thiopheneacetic acid

A technology of thiophene acetic acid and thiophene acetonitrile, applied in the direction of organic chemistry and the like, can solve the problems of difficult industrial production, low product yield and the like, and achieve the effects of mild reaction conditions, high safety performance and favorable industrial production.

Inactive Publication Date: 2017-03-22
LUDONG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(5) Chinese patent 200510047449 invented a method for synthesizing 2-thiopheneacetic acid from thiophene and glyoxylic acid. This method requires dehydration of raw materials and the use of metal catalysts. The product yield is low and it is not easy for industrial production

Method used

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  • Green preparation technology of 2-thiopheneacetic acid

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Embodiment 1

[0016] (1) Synthesis of 2-thiophene acetonitrile: Put 102.1g of acetone cyanohydrin, 150mL of ethanol, and 8.2g of triethylamine into a flask, heat up to 60-65°C, add 133.2g of 2-chloromethylthiophene, methyl iso Add 200mL of butyl ketone mixture slowly, keep it warm for 6 hours, then add 250mL of purified water, let stand to separate the organic phase after cooling slightly; the organic phase is distilled under reduced pressure to remove the organic solvent, and then further distilled to obtain 112.6 g of 2-thiophene acetonitrile, yield 91.5%.

[0017] (2) Synthesis of 2-thiopheneacetic acid: Heat 150g of 30% sodium hydroxide aqueous solution to reflux, then slowly add 112g of 2-thiopheneacetonitrile dropwise, and then reflux for 3 hours (there is a large amount of ammonia gas during the reaction produce). After the reaction is complete, lower the temperature to 20-30°C, and then use 200mL of ethyl acetate to extract impurities three times. After the extraction is complete,...

Embodiment 2

[0019] (1) Synthesis of 2-thiophene acetonitrile: put 102.6g of acetone cyanohydrin, 150mL of ethanol, and 11.5g of potassium carbonate into a flask, heat up to 60-65°C, and mix 133.3g of 2-chloromethylthiophene, methyl isobutyl methyl Add 200mL of the ketone mixture slowly, and keep it warm for 7 hours after the dropwise addition, then add 250mL of purified water, let it stand to separate the organic phase after cooling slightly; the organic phase is distilled under reduced pressure to remove the organic solvent, and then further distilled to obtain 2 - Thiophene acetonitrile 112.1g, yield 91.2%.

[0020] (2) Synthesis of 2-thiopheneacetic acid: Heat 150g of 30% sodium hydroxide aqueous solution to reflux, then slowly add 113g of 2-thiopheneacetonitrile dropwise, and then reflux for 2 hours after the drop (a large amount of ammonia gas is produced during the reaction process) ). After the reaction is complete, lower the temperature to 20-30°C, and then use 200mL of ethyl ace...

Embodiment 3

[0022] (1) Synthesis of 2-thiophene acetonitrile: Put 102.6g of acetone cyanohydrin, 150mL of ethanol, and 10.1g of triethylamine into a flask, raise the temperature to 60-65°C, add 133.3g of 2-chloromethylthiophene, methyl iso Add 200mL of butyl ketone mixture slowly, keep it warm for 10 hours after the addition, then add 250mL of purified water, let stand to separate the organic phase after cooling slightly; the organic phase is distilled under reduced pressure to remove the organic solvent, and further distilled to obtain 113.3 g of 2-thiophene acetonitrile, yield 92.1%.

[0023] (2) Synthesis of 2-thiopheneacetic acid: Heat 150g of 30% sodium hydroxide aqueous solution to reflux, then slowly add 113g of 2-thiopheneacetonitrile dropwise, and then reflux for 5 hours after the drop (a large amount of ammonia gas is produced during the reaction process) ). After the reaction is complete, lower the temperature to 20-30°C, and then use 200mL of ethyl acetate to extract impuriti...

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Abstract

The invention discloses a synthesis technology of 2-thiopheneacetic acid. The technology comprises the steps that 2-chloromethyl thiophene is taken as a raw material and reacts with acetone cyanohydrin in the presence of an organic solvent under the condition of a catalyst triethylamine to generate 2-thiopheneacetonitrile; 2-thiopheneacetonitrile is subjected to a series of reactions to generate 2-thiopheneacetic acid. The synthesis technology has the advantages that by selecting acetone cyanohydrin as a cyaniding reagent, usage of an extremely toxic substance sodium cyanide is avoided, the reaction yield is increased, the product quality is improved, the safety performance is relatively high, and industrialized production is promoted; the reaction conditions are mild, a little quantity of the catalyst is needed, and the processes are simple. Compared with an existing synthesis technology, the synthesis technology achieves the obvious economic benefits and environmental benefits.

Description

technical field [0001] The invention relates to a synthesis process of 2-thiopheneacetic acid, which belongs to the technical field of fine chemicals. Background technique [0002] 2-thiopheneacetic acid is currently the most widely used thiophene series derivative, widely used in the synthesis of fuels, pesticides, medicines, especially cephalosporins, such as the synthesis of broad-spectrum antibacterial drugs cephalothin, cefotaxime, and cefoxitin. [0003] The reported synthetic methods of 2-thiopheneacetic acid all use thiophene as raw material, adopt multi-step synthetic process, and finally obtain the product. The main types are as follows: (1) German Patent No. 832755 discloses that thiophene is acetylated, then undergoes Willgerodt reaction to generate 2-thiopheneacetamide, and then hydrolyzes to obtain 2-thiopheneacetic acid. However, this process requires high pressure and excess sulfur, and the target product yield is only 20.9%. (2) British Patent No.1122658 r...

Claims

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Application Information

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IPC IPC(8): C07D333/24
CPCC07D333/24
Inventor 王伟立任小亮宋燕萍陈厚
Owner LUDONG UNIVERSITY
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