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Method for synthesizing P-methylsulfonyl benzaldehyde

A technology based on methylmercaptobenzaldehyde and p-methylsulfone, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as low product yield and long reaction time, and achieve high selectivity and high product quality. Stable quality and obvious catalytic effect

Active Publication Date: 2014-05-28
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, in the existing synthetic methods, heteropolyacids, solid acids or ionic liquids are used as catalysts, and a kettle reaction process is adopted, the reaction time is long and the product yield is low

Method used

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  • Method for synthesizing P-methylsulfonyl benzaldehyde
  • Method for synthesizing P-methylsulfonyl benzaldehyde

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Experimental program
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Effect test

Embodiment 1

[0017] Two constant-flow pumps (Series II digital pumps, Chrom Tech, Inc.) were used to control the output of the raw material p-methylmercaptobenzaldehyde solution and hydrogen peroxide solution, so that the hydrogen peroxide solution and the p-methylmercaptobenzaldehyde solution were passed into the microreactor at the same time. The methylmercaptobenzaldehyde solution inlet and the hydrogen peroxide inlet are in contact with each other in the microreactor to initiate an oxidation reaction.

[0018] Microreactor:

[0019] CNC precision machining preparation

[0020] Material 316L stainless steel

[0021] Hydraulic diameter 0.4mm

[0022] Effective volume 230μl

[0023] Process conditions:

[0024] p-methylmercaptobenzaldehyde solution (p-methylmercaptobenzaldehyde 30wt.%, ethanol 70wt.%)

[0025] Hydrogen peroxide solution (hydrogen peroxide 30wt.%, sodium tungstate 4wt.%, sulfuric acid 0.6wt.%, water 65.4wt.%)

[0026] Microreactor temperature control 60°C

[0027] r...

Embodiment 2

[0039] Embodiment 2, solvent changes in p-methylmercaptobenzaldehyde solution

[0040] According to the same method of embodiment 1, the solvent in the p-methylmercaptobenzaldehyde solution is changed to methanol, and other experimental conditions and analysis methods are the same as in implementation 1. Implementation results: 95.0% p-methylsulfonyl benzaldehyde, 5.0% p-methylsulfinyl benzaldehyde, 0% p-methylmercaptobenzaldehyde.

Embodiment 3

[0041] Embodiment 3, reaction time changes in the microreactor

[0042] According to the same method of embodiment 1, the reaction time in the microreactor is changed to 2min, and other experimental conditions and analysis methods are identical with implementation 1. Implementation results: 94.5% p-methylsulfonyl benzaldehyde, 5.5% p-methylsulfinyl benzaldehyde, 0 p-methylmercaptobenzaldehyde.

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Abstract

The invention provides a novel method for synthesizing P-methylsulfonyl benzaldehyde. The method comprises the following steps: continuously pumping a P-methylthio benzaldehyde solution and a hydrogen peroxide solution into a micro-reactor and reacting at a temperature of 40-80 DEG C. The P-methylthio benzaldehyde solution comprises the following components: (a) P-methylthio benzaldehyde; (b) methanol or ethanol. The hydrogen peroxide solution comprises the following components: (a) hydrogen peroxide; (b) inorganic acid; (c) sodium tungstate. The method has the advantages that the P-methylsulfonyl benzaldehyde is continuously synthesized, the reaction time is short, the process is safe and controllable, the P-methylthio benzaldehyde raw material is fully converted, and the yield of the P-methylsulfonyl benzaldehyde product under optimized conditions is 97%.

Description

technical field [0001] The invention relates to a new method for synthesizing p-thiamphenicol benzaldehyde. Background technique [0002] P-thiamphenicol benzaldehyde is the starting material for the production of thiamphenicol, as well as the production of β-lactam antibacterial agents, fluorescent whitening agents, dihydropyridine derivatives antiangina drugs, and anti-inflammatory and anti-rheumatic drugs, etc. important intermediates. [0003] The current industrial method (Wang Feiwu et al., Modern Applied Pharmacy, 1991, 8 (5), 18) uses toluene as raw material, and "five-step reaction method" produces p-thiamphenicol benzaldehyde, that is, toluene reacts with chlorosulfonic acid to obtain p- Toluenesulfonyl chloride, p-toluenesulfonyl chloride reacts with sodium sulfite and sodium bicarbonate to obtain p-toluenesulfinic acid sodium salt, p-toluenesulfinic acid sodium salt reacts with dimethyl sulfate to obtain p-thiamphenyl toluene, p-thiamphenicol toluene and Liquid...

Claims

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Application Information

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IPC IPC(8): C07C317/24C07C315/02
Inventor 陈光文陈毅征韩梅
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI