Preparation method of 4-methylsulphonylphenylacetic acid

A technology of methylsulfonylbenzene and acetic acid, which is applied in the field of synthesis of 4-methylsulfonylphenylacetic acid, can solve the problems of large environmental pollution, and achieve the effects of extensive material sources, personnel injury and environmental damage

Inactive Publication Date: 2018-01-09
孙家强
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The present invention is a synthetic route provided for the problem of large environmental pollution in the existing synthetic routes

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 4-methylsulphonylphenylacetic acid
  • Preparation method of 4-methylsulphonylphenylacetic acid
  • Preparation method of 4-methylsulphonylphenylacetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 4-Methylthiobenzaldehyde

[0030] Add 150mL of DMF and 100.0g of thioanisole to a 500mL dry three-necked flask, cool to -5°C -5°C, slowly add 150.0g of phosphorus oxychloride dropwise, and keep the internal temperature at -5°C to 5°C during the dropwise addition between. After the dropwise addition, slowly increase the reaction temperature to 35-45°C, stir the reaction for 7 hours, and detect the reaction by TLC. After the reaction was completely completed, the reaction liquid was cooled to room temperature, and the reaction liquid was slowly added to 500 mL of ice water, and the temperature was kept not higher than 35°C. After the transfer is completed, stir at no higher than 35°C for 10 minutes, add 200 mL of dichloromethane, adjust the pH to 7-8 with 10% sodium hydroxide, separate the organic phase, continue to extract once with 200 mL of dichloromethane, and combine The organic phase was dried with anhydrous sodium sulfate, filtered, the organic sol...

example 2

[0031] Example 2: Preparation of 4-methylthiophenylacetaldehyde

[0032] Add 50mL of methyl α-chloroacetate to a 500mL dry three-necked flask, add 100.0g of 4-methylthiobenzaldehyde, cool the reaction solution to 0-10°C, slowly add 40mL of 27-30% sodium methoxide solution, drop After the addition is completed, gradually increase the reaction temperature to 25-30°C, and stir the reaction at this temperature for 3 hours, add 50mL of 20% sodium hydroxide solution, increase the reaction temperature to 55-60°C, hydrolyze for 2 hours, and Next, hydrochloric acid was added dropwise, and a large amount of gas was generated during the dropwise addition. After adding dropwise until no gas was generated, the reaction solution was cooled to room temperature, extracted three times with 300 mL of ethyl acetate, and the organic layers were combined.

[0033] Add anhydrous magnesium sulfate to the organic layer to dry, filter, and distill. When 200 mL remains, add 500 mL of n-heptane, contin...

example 3

[0034] Example 3: Preparation of 4-methylthiophenylacetaldehyde

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention belongs to the field of organic synthesis. The invention provides a method for preparing 4-methylsulfonylphenylacetic acid. The synthetic method is to use thioanisole as a starting material to obtain 4-methylthiobenzaldehyde through Vilsmeier reaction, and after Darzen reaction, 4-methylthiobenzaldehyde is hydrolyzed and decarboxylated to obtain 4-methylthiobenzaldehyde aldehyde. 4‑Methylthiophenylacetaldehyde is oxidized to give 4‑Methylsulfonylphenylacetic acid.

Description

field of invention [0001] The invention relates to a preparation method for synthesizing 4-methylsulfonylphenylacetic acid, which belongs to the field of organic synthesis. Background technique [0002] Etoricoxib is a selective cyclooxygenase inhibitor developed by Merck, which has anti-inflammatory, analgesic and antipyretic effects. This product is currently on the market in more than 80 countries around the world. The global API demand is about 100 tons. [0003] 4-Methanesulfonylphenylacetic acid (compound 1) is the key intermediate for the preparation of etoricoxib. The traditional method is to use thioanisole (compound 2) as the starting material, undergo Frid-Craft acylation reaction, Willgerodt-kindler rearrangement reaction, hydrolysis reaction, and finally oxidation, a total of four steps of chemical reaction to obtain 4-methylsulfonyl Phenylacetic acid. [0004] [0005] The method has the advantages of low synthesis cost, high yield, and low requirements ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/20C07C323/22C07C315/02C07C317/44C07D301/02C07D303/48
Inventor 孙家强
Owner 孙家强
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap