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Synthetic method of 4-methylsulfonyl methylbenzene

A methanesulfonyltoluene and synthesis method technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of reduced yield, poor atom economy, complicated by-products, etc., and achieve simplified production equipment and Process operation, solving the effect of poor atom economy and improving product yield

Active Publication Date: 2016-05-11
江西扬帆新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw materials of this process are cheap and easy to obtain, but dimethyl sulfate is a highly toxic substance under control, and the reaction process requires a large amount of alkali destruction, a large amount of waste water, poor atom economy, and the highest yield is only 65%.
Specifically: in this method, the alkali is NaOH, which is mainly used to destroy the structure of dimethyl sulfate; and after the reaction is completed, the by-products are complicated and the processing is cumbersome
In this method, if NaOH is changed into sodium bicarbonate, the yield will be greatly reduced

Method used

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  • Synthetic method of 4-methylsulfonyl methylbenzene
  • Synthetic method of 4-methylsulfonyl methylbenzene
  • Synthetic method of 4-methylsulfonyl methylbenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1, a kind of synthetic method of 4-methylsulfonyltoluene, carry out following steps successively:

[0054] 1), set two 250mL autoclave (autoclave I and autoclave II), these two autoclave respectively carry out exactly the same step 1); The molar weights of phenylsulfonyl chloride are exactly the same;

[0055] details as follows:

[0056] Add 12.6g of sodium sulfite (molecular weight 126, 0.1mol), 60mL of water, and about 16.0g of sodium bicarbonate into a 250mL autoclave with a stirring temperature measuring device to adjust the pH of the solution to 8, close the lid of the kettle, and insert condensed water ;

[0057] Use N 2 Check for leaks, turn on the stirring and heating device, and slowly raise the temperature of the reaction solution to 75-80°C; melt the raw material 4-methylbenzenesulfonyl chloride (around 70°C), and use a feed pump to feed slowly, 4.3g each time , 20min / time, feeding 4 times (a total of 17.2g, 0.09mol);

[0058] After the feedi...

Embodiment 14

[0074] Replace "60mL water, 16g sodium bicarbonate" in step 1) with "60mL water, 16g sodium bicarbonate" in the step 1) of "the filtrate II obtained by adding ice-out salt and filtering in the filtrate I" in step 5) of embodiment 1, and the remaining contents are equal to embodiment 1.

[0075] The final result obtained was: 13.2 g of the product 4-methylsulfonyltoluene was obtained, the yield was 86.3%, and the purity detected by HPLC was 99.5%.

[0076] Comparative example 1-1, change " methyl chloride " in embodiment 1 into " dimethyl sulfate " (molar weight is unchanged) carry out methylation reaction, all the other contents are equal to embodiment 1.

[0077] The final result obtained was: 8.0 g of the product 4-methylsulfonyltoluene was obtained, the yield was 52.4%, and the purity detected by HPLC was 99%.

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Abstract

The invention discloses a synthetic method of 4-methylsulfonyl methylbenzene. The method comprises the following steps in sequence: by taking 4-toluene sulfonyl chloride as a start material, feeding through fusion, performing a reduction reaction between the 4-toluene sulfonyl chloride and sodium sulfite in an alkali aqueous solution so as to generate sodium 4-methyl benzene sulfinate; performing a methylation reaction between the sodium 4-methyl benzene sulfinate and chloromethane, enabling a reaction product to be subjected to the post treatment such as filtration and recrystallization to obtain the product 4-methylsulfonyl methylbenzene. According to the invention, chlorosulfonyl is converted into methylsulfonyl in a one-pot manner; production equipment and technological operation are simplified, the loss brought about by material transfer is reduced, and the product yield is improved.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 4-methylsulfonyltoluene. Background technique [0002] 4-Methanesulfonyltoluene, formula C 8 h 10 o 2 S, CAS No. 3185-99-7, molecular weight 170.0, melting point 84-89°C, boiling point 311.7°C, structural formula as shown in S-1. [0003] [0004] 4-Methylsulfonyltoluene is the main raw material of p-thymphenylphenylserine ethyl ester, which is an important intermediate for the production of thiamphenicol and fluprofen. At the same time, it is also a kind of acaricidal drug, which can control various mites in cotton, fruit trees, vegetables and other crops. [0005] There are mainly three kinds of synthetic techniques of 4-methylsulfonyltoluene reported in the literature at present. Respectively with toluene, 4-methylthiophenol, 4-methylbenzenesulfonyl chloride as initial raw materials, specifically as follows: [0006] (1) Document (Pey...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/14C07C315/00
CPCC07C313/04C07C315/00C07C317/14
Inventor 樊彬王玲陶明陈育亮吕雪皓廖祖态
Owner 江西扬帆新材料有限公司
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