Preparation method of p-methylsulfonyl benzaldehyde

A technology for p-methylsulfonyl and p-chlorobenzaldehyde is applied in the preparation of thiamphenicol pharmaceutical intermediates and in the field of preparation of pharmaceutical intermediates. The effect of short production cycle, short reaction route and easy operation

Active Publication Date: 2012-09-19
SHANDONG HANXING PHARM TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process has a long reaction route, low yield, high unit consumption, low utilization rate of equipment, cumbersome operation, and high pressure on environmental protection, which is not conducive to industrial production
[0006] Dong Shunkang et al. reported in "China Pharmaceutical Industry Journal" 1979, 05, pages 1-3 that p-toluenesulf

Method used

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  • Preparation method of p-methylsulfonyl benzaldehyde
  • Preparation method of p-methylsulfonyl benzaldehyde
  • Preparation method of p-methylsulfonyl benzaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] According to p-chlorobenzaldehyde: sodium methylmercaptide: the mol ratio of tetrabutylammonium bromide is 1: 1.1: 0.025 and carries out following reaction:

[0033] Under stirring conditions, add 20% by mass concentration of sodium methyl mercaptide aqueous solution, tetrabutylammonium bromide, and 250g p-chlorobenzaldehyde to the reaction kettle, control the temperature at 45-50°C for reaction, and monitor the reaction by TLC until p-chlorobenzaldehyde The reaction of benzaldehyde was complete, and the layers were separated after standing to obtain 290 g of yellow oil in the lower layer, and the yield of crude p-methylthiobenzaldehyde was 107.2%.

[0034] According to p-methylthiobenzaldehyde: hydrogen peroxide: sulfuric acid: the mol ratio of sodium tungstate is 1: 2.5: 0.02: 0.015 and proceeds as follows:

[0035] Under stirring, add 50% concentration of hydrogen peroxide, sodium tungstate and sulfuric acid into the reaction kettle, raise the temperature to 40-50°C,...

Embodiment 2

[0039] According to p-chlorobenzaldehyde: sodium methylmercaptide: tetrabutylammonium chloride mol ratio is 1: 2: 0.2 and carry out following operations:

[0040] Add 250g of p-chlorobenzaldehyde, 30% aqueous solution of sodium methyl mercaptide and tetrabutylammonium chloride into the reaction kettle under stirring, raise the temperature to 55-60°C for reaction, monitor by TLC, until the reaction of p-chlorobenzaldehyde is complete, let stand Separate layers to obtain 296 g of yellow oil in the lower layer, and the yield of crude p-methylthiobenzaldehyde is 109.4%.

[0041] According to p-methylthiobenzaldehyde: hydrogen peroxide: sulfuric acid: manganese sulfate mol ratio is 1: 2.5: 0.02: 0.05 and carries out following operations:

[0042] Add 20% concentration of hydrogen peroxide, manganese sulfate and concentrated sulfuric acid into the reaction kettle, stir and heat up to 40-45°C, add the whole batch of crude p-methylthiobenzaldehyde dropwise, control the reaction temper...

Embodiment 3

[0044] According to p-chlorobenzaldehyde: sodium methylmercaptide: tetrabutylammonium iodide mol ratio is 1: 1.5: 0.1 and carry out following operation:

[0045] Add 250g of p-chlorobenzaldehyde, 15% aqueous solution of sodium methyl mercaptide and tetrabutylammonium chloride into the reaction kettle under stirring, raise the temperature to 50-55°C for reaction, monitor by TLC, until the reaction of p-chlorobenzaldehyde is complete, let stand Separate layers to obtain 288 g of yellow oil in the lower layer, and the yield of crude p-methylthiobenzaldehyde is 106.5%.

[0046] According to p-methylthiobenzaldehyde: hydrogen peroxide: sulfuric acid: manganese sulfate mol ratio is 1: 4: 0.1: 0.1 carries out following operation:

[0047] Add 30% concentration of hydrogen peroxide, manganese sulfate and concentrated sulfuric acid into the reaction kettle, stir and heat up to 40-45°C, add the whole batch of crude p-methylthiobenzaldehyde dropwise, control the reaction temperature at 5...

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Abstract

The invention discloses a preparation method of p-methylsulfonyl benzaldehyde, which takes p-chlorobenzaldehyde as starting material, and comprises the steps of: enabling the starting material to have reaction with sodium methyl mercaptide water solution under the action of phase transfer catalyst to obtain p-methylthio benzaldehyde; and oxidizing the p-methylthio benzaldehyde by hydrogen peroxide under the action of sulfuric acid and oxidation catalyst to obtain the p-methylsulfonyl benzaldehyde. The preparation method is easy in obtaining of raw material of the p-methylsulfonyl benzaldehyde, simple and convenient in operation, low in cost, high in yield and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of a thiamphenicol pharmaceutical intermediate, and belongs to the field of organic chemistry. Background technique [0002] p-thymphenylbenzaldehyde, CAS No.5398-77-6, molecular structure: [0003] [0004] It is the main intermediate for the production of a new generation of broad-spectrum antibiotic thiamphenicol and its amino compounds. [0005] The existing process uses toluene as a raw material, and undergoes steps such as chlorosulfonation, reduction, methylation, bromination, and hydrolysis to obtain p-thiamphenicol benzaldehyde. The process has a long reaction route, low yield, high unit consumption, low utilization rate of equipment, cumbersome operation and high environmental protection pressure, which is unfavorable for industrialized production. [0006] Dong Shunkang et al. reported in "China Pharmaceutical Industry J...

Claims

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Application Information

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IPC IPC(8): C07C317/24C07C315/02
Inventor 刘伟军王立新张从金徐小英周敦峰刘良有武强阎素花张康华
Owner SHANDONG HANXING PHARM TECH CO LTD
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