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Preparation of 2-[2-(thienyl) vinyl] benzoic acid

A vinyl and benzoic acid technology, applied in organic chemistry, etc., can solve the problems of low yield and cumbersome steps, and achieve the effects of high product yield, good reactivity, and simple method

Inactive Publication Date: 2009-07-08
浙江工业大学浙西分校
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Heterocyclic compounds (vol.7, No.5, 2001), reported a method using methyl o-toluate as a raw material, through free radical reaction, and then through Arbuzov rearrangement reaction to obtain phosphonate and then react with 2 - Thiophene formaldehyde is obtained through Horner reaction, and the method steps are comparatively loaded down with trivial details, and yield is lower, only 52.5% in total

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 0.5 mol of dimethyl o-cyanobenzylphosphonate, 0.5 g of 2-thiophene carboxaldehyde and 80 ml of DMAC into the three-necked flask, drop 90 ml of 10% sodium methoxide methanol solution within 2 hours, react at 10°C for 30 hours, pour 200 ml of ice Water, recrystallized to dark brown crystals. Add ethanol, 50ml of water, and 20g of potassium hydroxide, heat to 60°C for 85h, adjust the pH value of the reaction solution to 3-4, a brown solid precipitates, and recrystallizes to obtain light brown crystals. The total yield is 88%.

Embodiment 2

[0018] Add 0.5mol of diethyl o-cyanobenzylphosphonate, 0.75mol of 2-thiophenecarbaldehyde and 120ml of DMF into a three-necked flask, add 80ml of 30% ethanol solution of sodium hydroxide dropwise within 1 hour, react at 30°C for 10 hours, pour 500ml of ice into Water, recrystallized to dark brown crystals. Add ethylene glycol, 150ml of water, 50g of sodium hydroxide, heat at 100°C, reflux for 60h, adjust the pH value of the reaction solution to 3-4, a brown solid precipitates, and recrystallizes to obtain a light brown crystal. The total yield is 85%.

Embodiment 3

[0020] Add 0.5mol of diisopropyl o-cyanobenzylphosphonate, 0.65mol of 2-thiophene carboxaldehyde and 120ml of DMI into a three-necked flask, drop 30% sodium isopropoxide and isopropanol solution within 10 hours, react at 30°C for 10 hours, pour into In 500ml of ice water, dark brown crystals were obtained. Add 50g of isopropanol and 50ml of water, react at 78°C for 24h, adjust the pH to 3-4, precipitate brown solids, and recrystallize to obtain light brown crystals. The total yield is 79%.

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PUM

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Abstract

The invention provides a method for preparing 2-[2-(thienyl) vinyl] benzoic acid. The method uses o-cyanobenzyl phosphate as a raw material to prepare the 2-[2-(thienyl) vinyl] benzoic acid through two steps of condensation and hydrolysis. Compared with the prior preparation method, the method has the characteristics of low-price and easily-available raw materials, mild conditions, high yield, lower production cost and the like and is suitable for industrial production.

Description

【Technical field】 [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of 2-[2-(thienyl)vinyl]benzoic acid. 【Background technique】 [0002] 2-[2-(thienyl)vinyl]benzoic acid (2-[2-(thienyl)vinyl]benzoic acid) is an important intermediate in the synthesis of antihistamines ketotifen and phenylthiazine. [0003] Before the present invention was made, the main method was to use 2-chloromethylthiophene as raw material and triethyl phosphite to obtain phosphonate through Arbuzov rearrangement reaction, and then generate Horner reaction with o-carboxybenzaldehyde. The raw material 2-chloromethylthiophene used in this method is unstable in nature, not suitable for long-term storage, flammable and explosive, unfavorable for industrial production, and the price of o-carboxybenzaldehyde is relatively high. The total yield is only 28.7%-33.3%. Heterocyclic compounds (vol.7, No.5, 2001), reported a method using meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24
Inventor 谢艳郑土才谢建伟程慎玉
Owner 浙江工业大学浙西分校