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A kind of one-pot synthesis method of m-acetylbenzoic acid

A technology of acetylbenzoic acid and synthesis method, applied in chemical instruments and methods, preparation of carboxylate, preparation of carboxylate, etc., can solve problems such as being difficult to be suitable for industrial production, unstable in nature, potential safety hazards, etc., and achieve cheap raw materials. Easy availability, reduced process cost, mild reaction conditions

Inactive Publication Date: 2017-10-13
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantage is that m-cyanoacetophenone is expensive and rare, and it needs to use highly toxic substance cuprous cyanide and noble metal Pd catalyst in its preparation process
Cuprous cyanide is generally produced by the reaction of sodium cyanide (or potassium) and cuprous salt, and its properties are also unstable. It can release highly toxic gas when it absorbs water in the air, and there is a great potential safety hazard. Suitable for industrial production

Method used

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  • A kind of one-pot synthesis method of m-acetylbenzoic acid
  • A kind of one-pot synthesis method of m-acetylbenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 20g of isophthalic acid, 3 drops of DMF and 300ml of toluene to a 500ml three-necked reaction flask in sequence, raise the temperature to about 60°C, add 22ml of thionyl chloride dropwise, raise the temperature and reflux for 1 hour until no bubbles come out, steam the excess under normal pressure SOCl 2 and part of toluene (recovered and used mechanically), then cooled to room temperature, added 16.6ml triethylamine to the reaction bottle, stirred evenly, added dropwise 4.8ml methanol to the bottle, stirred for 1h after the dropwise addition, and TLC detected that the reaction was complete to obtain A solution of monomethyl formyl chloride. Add 33.4ml triethylamine, 14.4gCaCl successively under stirring 2 powder and 22ml of diethyl malonate, stir at room temperature for 1h after the addition, TLC detects that the reaction is complete, then add 50ml of 3mol / L hydrochloric acid to the reaction bottle to adjust the pH to about 1, separate the organic phase, concentra...

Embodiment 2

[0034] Add 40g of isophthalic acid, 3 drops of DMF and 300ml of toluene to a 500ml three-necked reaction flask in sequence, raise the temperature to about 60°C, add 44ml of thionyl chloride dropwise, raise the temperature and reflux for 1 hour until no bubbles come out, steam the excess at normal pressure SOCl 2 and part of toluene (recovery for mechanical use), then cooled to room temperature, 33.4ml triethylamine was added in the reaction bottle, after stirring evenly, 9.5ml n-propanol was added dropwise in the bottle, and after the dropwise addition was completed and stirred for 1h, TLC detected that the reaction was complete, and obtained A solution of m-benzoyl chloride mono-n-propyl ester. Add 66.8ml triethylamine, 28.8g CaCl 2Powder and 44ml of dimethyl malonate, stirred at room temperature for 1h after the addition was completed, TLC detected the completion of the reaction, then added 80ml of 3mol / L hydrochloric acid to the reaction bottle to adjust the pH to about 1,...

Embodiment 3

[0036] Add 60g of isophthalic acid, 6 drops of DMF and 400ml of toluene to a 1000ml three-necked reaction flask in sequence, raise the temperature to about 60°C, add 66ml of thionyl chloride dropwise, raise the temperature and reflux for 1 hour until no bubbles come out, steam the excess under normal pressure SOCl 2 and part of toluene (recovered and used mechanically), then cooled to room temperature, 50ml of triethylamine was added to the reaction bottle, after stirring evenly, 14.4ml of methanol was added dropwise to the bottle, and the dropwise addition was completed and stirred for 1h. TLC detected that the reaction was complete, and m-benzylbenzene was obtained. A solution of monomethyl chloride. Add 90ml triethylamine, 90g CaBr successively under stirring 2 Powder and 22ml of diethyl malonate, stir at room temperature for 1 hour after the addition is complete, TLC detects that the reaction is complete, then add 150ml of 3mol / L hydrochloric acid to the reaction bottle t...

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Abstract

The invention relates to a synthetic method, in particular to a one-pot synthetic method for m-acetylbenzoic acid. According to the one-pot synthetic method for the m-acetylbenzoic acid, there is no need to purify an intermediate product. The reaction equation of the m-acetylbenzoic acid is shown in the description, wherein R refers to methyl or ethyl, and R1 refers to methyl or ethyl or n-propyl. Compared with synthetic methods in the prior art, the synthetic method has the advantages that raw materials are low in price and easy to get, reaction conditions are mild, the obtained intermediate product can be directly used for a reaction in a next step without being separated and purified, and therefore process cost is greatly lowered.

Description

technical field [0001] The invention relates to a synthesis method, in particular to a one-pot synthesis method of m-acetylbenzoic acid. Background technique [0002] m-Acetobenzoic acid is a white solid powder, it is the main intermediate in the synthesis of ketoprofen [JP55007225], the latter is the main antipyretic, analgesic and anti-inflammatory drug in the market today, with significant advantages such as high efficiency and low toxicity . The preparation method of m-acetylbenzoic acid reported in literature now mainly contains two kinds: [0003] Method 1: Japanese patent JP2050072 uses dimethyl isophthalate as a raw material to undergo Claisen condensation reaction with ethyl acetate under the action of strong alkali NaH to form a ketone ester, and then heats and hydrolyzes and decarboxylates under the action of hydrochloric acid to obtain m-acetylbenzoic acid , but there are many by-products, which are not easy to separate and purify, and the yield is low, only ab...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/09C07C51/38C07C65/32
CPCC07C51/09C07C51/38C07C51/60C07C67/14C07C67/343C07C63/24C07C69/76C07C65/32
Inventor 朱锦桃石亚磊吴江周俊鹏李扬
Owner ZHEJIANG SCI-TECH UNIV
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