Method for synthesizing benzoic acid compound from benzyl alcohol compound by ultrasonic-assisted oxidation

A technology for benzoic acids and compounds, which is applied in the field of organic intermediate synthesis, can solve the problems of incompatibility with alkali-sensitive functional groups, adverse environmental effects, and increase reaction costs, thereby reducing separation and purification costs, shortening reaction time, and low production costs. Effect

Inactive Publication Date: 2018-08-31
CENT SOUTH UNIV
View PDF2 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] (1) The three routes all use a large amount of strong base as a reaction accelerator. After the reaction, an excessive amount of protic acid needs to be added for acid-base neutralization treatment, which is incompatible with alkaline-sensitive functional groups, such as ester groups, cyano groups, etc.;
[0017] (2) Routes 1 and 3 need to use a large amount of organic solvents, which will cause adverse effects on the environment when increasing the reaction cost;
[0018] (3) Routes 2 and 3 require the use of noble metal catalysts and ligands, the reaction cost is high, and the problem of metal residues may occur in the synthesis of pharmaceutical intermediates

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
  • Method for synthesizing benzoic acid compound from benzyl alcohol compound by ultrasonic-assisted oxidation
  • Method for synthesizing benzoic acid compound from benzyl alcohol compound by ultrasonic-assisted oxidation
  • Method for synthesizing benzoic acid compound from benzyl alcohol compound by ultrasonic-assisted oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the preparation of benzoic acid:

[0068] Into a 10mL round-bottomed flask, add 0.54g (5mmoL) of benzyl alcohol and 2g (15mmoL) of diethylene glycol dimethyl ether in sequence. The resulting mixture is subjected to ultrasonic radiation at 40KHz / 30W / 70°C for 30 minutes in an ultrasonic reaction device. . Diethylene glycol dimethyl ether was removed under reduced pressure, and 0.59 g of the corresponding benzoic acid was obtained by recrystallization, with a yield of 98%.

[0069] Scale-up preparation:

[0070] 1L three-neck round bottom flask, the middle grinding port is connected to a mechanical stirrer, one grinding port is externally connected to an 80cm serpentine condenser, and one external port is connected to an air source. Add 54g of benzyl alcohol and 200g of diethylene glycol dimethyl ether in sequence, and the resulting mixture is ultrasonically In the reaction device, 40KHz / 80W / 70°C ultrasonic radiation was used for 50 minutes. Diethylene gly...

Embodiment 2

[0075] Compared with Example 1, the difference is that the conversion reaction temperature is 60°C, specifically as follows:

[0076] Into a 10mL round bottom flask, add 0.54g of benzyl alcohol and 2g of diethylene glycol dimethyl ether in sequence, and react the resulting mixture in an ultrasonic reaction device with ultrasonic radiation at 40KHz / 30W / 60°C for 30 minutes. Diethylene glycol dimethyl ether was removed under reduced pressure, and 0.35 g of benzoic acid was obtained by recrystallization, with a yield of 58%.

Embodiment 3

[0078] Into a 10 mL round bottom flask, add 0.54 g of benzyl alcohol and 2 g of diethylene glycol dimethyl ether in sequence, and react the resulting mixture in an ultrasonic reaction device under ultrasonic radiation at 17KHz / 30W / 70°C for 30 minutes. Diethylene glycol dimethyl ether was removed under reduced pressure, and 0.54 g of benzoic acid was obtained by recrystallization, with a yield of 88%.

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 synthesis of organic intermediates, and specifically discloses an ultrasonic-assisted synthesis method for a benzoic acid compound. The method comprises the following step: promoting air oxidation of benzyl alcohol by using diethylene glycol dimethyl ether under an ultrasonic-assisted action so as to obtain the benzoic acid compound, wherein a benzyl alcohol raw material is benzyl alcohol, or a benzoic acid derivative containing one to five substituents at different positions on the benzene ring of benzyl alcohol; and a reaction accelerator is the diethylene glycol dimethyl ether. The method provided by the invention has the advantages of easily-available raw materials, simple and convenient reaction conditions, short reaction time, greenness, energy conservation, high reaction selectivity and yield, excellent compatibility of substrate functional groups, and high application value.

Description

technical field [0001] The invention belongs to the technical field of organic intermediate synthesis, and in particular relates to a synthesis method of benzoic acid compounds. Background technique [0002] Benzoic acid is widely used in food, medicine, dyestuff and other chemical fields, and it is also an important class of organic synthesis intermediates. At present, a large number of literatures have reported the synthesis methods of benzoic acid, including: toluene liquid phase oxidation, benzonitrile hydrolysis, toluene chlorination hydrolysis, phthalic anhydride hydrolysis, alcohol oxidation and so on. [0003] Liquid-phase oxidation of toluene is currently the most important method for producing benzoic acid, which is usually produced by catalytic air oxidation of toluene with catalysts such as cobalt and manganese. However, this type of reaction has a low single conversion rate and requires multiple cycles of oxidation reactions. Functional group tolerance is limit...

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
IPC IPC(8): C07C51/235C07C63/06C07C63/04C07C63/331C07C65/03C07C65/21C07C63/70C07C63/26C07C201/12C07C205/57C07C253/30C07C255/57C07C67/313C07C69/82C07B41/08
CPCC07B41/08C07C51/235C07C67/313C07C201/12C07C253/30C07C63/06C07C63/04C07C63/331C07C65/03C07C65/21C07C63/70C07C63/26C07C205/57C07C255/57C07C69/82
Inventor 肖芳肖元元曾明李娜殷丽蓉
Owner CENT SOUTH UNIV
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