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A novel process for synthesizing a ketal intermediate of 2-(4'-bromomethyl)phenylpropionic acid

A technology of bromomethyl phenyl and intermediate, which is applied in the field of new technology for synthesizing 2-propionic acid intermediate ketal, can solve the problems of many three wastes, the yield needs to be improved, etc., and achieves high selectivity, high conversion rate, high reaction mild effects

Inactive Publication Date: 2016-04-06
WUHAN INSTITUTE OF TECHNOLOGY +1
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the four synthetic methods, the synthetic process using toluene as the starting material has the characteristics of cheap starting material, high yield, and simple process, but the ketal stage of the reaction needs to use relatively high-priced neopentyl glycol as protection. agent, and there are many three wastes, and the yield needs to be improved

Method used

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  • A novel process for synthesizing a ketal intermediate of 2-(4'-bromomethyl)phenylpropionic acid
  • A novel process for synthesizing a ketal intermediate of 2-(4'-bromomethyl)phenylpropionic acid
  • A novel process for synthesizing a ketal intermediate of 2-(4'-bromomethyl)phenylpropionic acid

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Experimental program
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Effect test

Embodiment 1

[0021] 18.251g (0.1mol) of 1-p-tolyl-2-chloro-1-propanone, 81.642g (0.8mol) of propylene carbonate, 0.086g (0.0005mol) of anhydrous p-toluenesulfonic acid, 0.032g ( 0.0001mol) of tetrabutylammonium bromide and 150ml of anhydrous toluene are placed in a reaction flask equipped with a water separator, stirred and refluxed for dehydration for 5h, cooled to room temperature, and the ketal yield by liquid chromatography analysis is 63.9% (based on 1-p-tolyl-2-chloro-1-propanone).

Embodiment 2

[0023] 18.252g (0.1mol) of 1-p-tolyl-2-chloro-1-propanone, 12.244g (0.12mol) of propylene carbonate, 3.451g (0.02mol) of anhydrous p-toluenesulfonic acid, 0.085g ( 0.0002mol) of octadecyldimethylbenzyl ammonium chloride and 100ml of anhydrous toluene are placed in a reaction flask equipped with a water separator, stirred and refluxed for dehydration for 42h, cooled to room temperature, and analyzed by liquid chromatography for ketal yield. The yield was 87.3% (calculated as 1-p-tolyl-2-chloro-1-propanone).

Embodiment 3

[0025] 18.248g (0.1mol) of 1-p-tolyl-2-chloro-1-propanone, 20.407g (0.2mol) propylene carbonate, 1.726g (0.01mol) anhydrous p-toluenesulfonic acid, 0.371g ( 0.001mol) of tetrabutylammonium iodide and 150ml of anhydrous toluene, placed in the reaction flask equipped with a water separator, stirred and refluxed for dehydration 20h, cooled to room temperature, liquid chromatography analysis ketal yield 96.4% (with 1 - calculated from p-tolyl-2-chloro-1-propanone).

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Abstract

The invention belongs to the technical field of chemical engineering and particularly relates to a novel process for synthesizing a ketal intermediate of 2-(4'-bromomethyl)phenylpropionic acid. The process adopts a ketone and a cyclic carbonate as raw materials and prepares the ketal intermediate by performing ketalation under catalysis of a catalyst. The mole ratio of the ketone to the cyclic carbonate is 1:1-10. The mole ratio of the ketone to the catalyst is 1:0.001-0.2. The cyclic carbonate is ethylene carbonate or propylene carbonate. The ketone is prepared by subjecting methylbenzene to acylation with 2-halogen propionyl halogenide and is 1-p-methylphenyl-2-chloro-1-propiophenone or 1-p-methylphenyl-2-bromo-1-propiophenone. The process is characterized by high selectivity, a high conversion ratio and mild reaction conditions, can meet requirements of industrial production processes, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, in particular to a new process for synthesizing 2-(4'-bromomethylphenyl)propionic acid intermediate ketal. Background technique [0002] Traditional non-steroidal anti-inflammatory drugs may cause serious gastrointestinal adverse reactions such as gastric ulcer, bleeding and perforation if taken for a long time. A British study found that the risk of ulcer complications such as gastric perforation or gastric bleeding caused by taking non-steroidal anti-inflammatory drugs was 3 to 5 times higher than that of the placebo treatment group. Studies in the United States have shown that in the United States, 107,000 patients are hospitalized each year due to upper gastrointestinal complications caused by taking NSAIDs, and 16,500 people die as a result. One of the most common causes of serious adverse drug reactions. [0003] Loxoprofen, Japan's Sankyo Co., Ltd. was listed under the trade na...

Claims

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Application Information

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IPC IPC(8): C07D317/16
CPCC07D317/16
Inventor 杜治平文武强李亮丁一刚邓伏礼刘生鹏龙秉文查树义
Owner WUHAN INSTITUTE OF TECHNOLOGY
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