Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of m-phenoxy benzaldehyde

A technology of m-phenoxybenzaldehyde and halobenzene is applied in the field of preparation of m-phenoxybenzaldehyde, can solve problems such as low yield and low purity of m-phenoxybenzaldehyde, and achieves reduction of production cost and simple process The effect of easy operation and cheap and easy to obtain raw materials

Active Publication Date: 2021-04-16
锦州三丰科技有限公司
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] For the preparation method of m-phenoxybenzaldehyde, the prior art all has the disadvantages of low purity and low yield of m-phenoxybenzaldehyde

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 m-phenoxy benzaldehyde
  • Preparation method of m-phenoxy benzaldehyde
  • Preparation method of m-phenoxy benzaldehyde

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0026] The invention provides a kind of preparation method of m-phenoxybenzaldehyde, comprising the following steps:

[0027] Performing a salt-forming reaction between m-hydroxybenzaldehyde and an alkaline reagent in an anhydrous organic solvent to obtain a salt-forming product reaction solution;

[0028] mixing the salt-forming product reaction liquid with halobenzene, performing a substitution reaction between the salt-forming product and halobenzene under alkaline conditions, and subjecting the obtained substitution reaction liquid to solid-liquid separation to obtain a liquid phase;

[0029] Fractional distillation is performed on the liquid phase, and fractions at 170-190° C. are collected to obtain the m-phenoxybenzaldehyde.

[0030] In the present invention, unless otherwise specified, the components in the preparation method are commercially available products well known to those skilled in the art.

[0031] In the invention, m-hydroxybenzaldehyde and alkaline reagen...

Embodiment 1

[0056] Mix 122.1g (1.0mol) of m-hydroxybenzaldehyde, 244mL of N,N-dimethylformamide and 165.8g (1.2mol) of anhydrous potassium carbonate, and control the pH value of the resulting mixed system to 12. Under heat preservation and stirring for 1h, carry out a salt-forming reaction to obtain a mixture containing an intermediate;

[0057] Under the condition of 90-100°C, 164.8g (1.05mol) of bromobenzene was added dropwise into the mixture at a rate of 2 drops / s, and the intermediate and halobenzene were kept and stirred at 90-100°C for 2 hours to carry out the substitution reaction. After the mixed system was cooled to 30°C, it was filtered, and the obtained filtrate was subjected to fractional distillation, and the fraction at 170-190°C was collected to obtain 160.5 g of m-phenoxybenzaldehyde.

[0058] The product obtained in this example is detected: mass spectrometry MS (ESI), m / z: 199.3 [M+H] + ;

[0059] NMR 1 H NMR (400MHz, CDCl 3 ), δ=7.22(2H, ArH), 6.98(H, ArH), 6.92(2H...

Embodiment 2

[0062] Mix 122.1g (1.0mol) of m-hydroxybenzaldehyde, 244mL of N-methylpyrrolidone and 165.8g (1.2mol) of anhydrous potassium carbonate, control the pH value of the resulting mixed system to 12, and keep stirring at 90-100°C for 1h Perform a salt-forming reaction to obtain a mixture containing intermediates;

[0063] Under the condition of 90-100°C, 164.8g (1.05mol) of bromobenzene was added dropwise into the mixture at a rate of 2 drops / s, and the intermediate and halobenzene were kept and stirred at 90-100°C for 2 hours to carry out the substitution reaction. After the mixed system was cooled to 30°C, it was filtered, and the resulting filtrate was subjected to fractional distillation, and the fraction at 170-190°C was collected to obtain 159.2 g of m-phenoxybenzaldehyde.

[0064] The present embodiment middle phenoxybenzaldehyde yield is 80.4%; The gas phase content GC of m-phenoxybenzaldehyde is 99.3%.

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 technical field of organic synthesis, and particularly relates to a preparation method of m-phenoxy benzaldehyde. According to the preparation method provided by the invention, m-hydroxybenzaldehyde is salified by phenolic hydroxyl under an alkaline anhydrous condition, and then is subjected to substitution reaction with halobenzene to obtain m-phenoxy benzaldehyde, so that disproportionation reaction of aldehyde groups during reaction in an alkaline aqueous solution is avoided, the utilization rate of raw materials is increased, and side reactions are reduced. The purification of the m-phenoxybenzaldehyde product and the improvement of the yield are facilitated. The test result of the embodiment shows that the yield of m-phenoxybenzaldehyde obtained by the preparation method provided by the invention is 79.9-81%, and the yield is high; the gas phase content of m-phenoxy benzaldehyde is 98.9%-99.3%, and the purity of m-phenoxy benzaldehyde is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of m-phenoxybenzaldehyde. Background technique [0002] m-phenoxybenzaldehyde, also known as 3-methoxybenzaldehyde and 3-formyl diphenyl ether, is an important intermediate for the synthesis of high-efficiency, broad-spectrum, safe and low-toxic pyrethroid pesticides. Meta-phenoxybenzaldehyde is light yellow liquid, insoluble in water, soluble in alcohol, benzene, the synthetic method of the meta-phenoxybenzaldehyde of current report has following several: [0003] (1) Take benzaldehyde as a raw material, react with bromine to m-bromobenzaldehyde, then condense with phenol under alkaline conditions to obtain product m-phenoxybenzaldehyde (He Jingyan, Guo Henan, Xu Chunmei, m-phenoxybenzaldehyde Synthesis of Pesticides [J], 1989,28(1):13-14.). A small amount of p-bromobenzaldehyde is generated when the first step of this method is subst...

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): C07C47/575C07C45/64C07C45/82C07C47/565C07C45/61
CPCY02P20/55
Inventor 王栋伟赵宏洋王诚刘涛
Owner 锦州三丰科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com