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Preparation method of m-phenoxy benzaldehyde

A technology of m-phenoxybenzaldehyde and m-phenoxytoluene, applied in the field of preparation of m-phenoxybenzaldehyde, can solve the problems of high cost and low product yield

Pending Publication Date: 2021-04-16
锦州三丰科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In summary, there are generally problems of low product yield and high cost in the preparation of m-phenoxybenzaldehyde in the prior art

Method used

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

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

[0027] Mix m-cresol, halogenated benzene, inorganic base and catalyst for condensation reaction to obtain m-phenoxytoluene;

[0028] The m-phenoxytoluene is mixed with an oxidizing agent, and an oxidation reaction is carried out under acidic conditions to obtain m-phenoxybenzaldehyde.

[0029] In the present invention, unless otherwise specified, the raw materials used are commercially available products well known in the art.

[0030] In the invention, m-cresol, halogenated benzene, inorganic base and catalyst are mixed for condensation reaction to obtain m-phenoxytoluene.

[0031] In the present invention, the halogenated benzene is preferably chlorobenzene, bromobenzene or fluorobenzene, more preferably chlorobenzene; the molar ratio of m-cresol and halogenated benzene is preferably 1:(2~3), more preferably Preferably 1:2.

[0032] In the present inventi...

Embodiment 1

[0045] The reaction equation of embodiment 1 is as follows:

[0046]

[0047] (1) Preparation of m-phenoxytoluene: 1000mL four-necked bottle is installed with stirring, thermometer and water separator, add m-cresol 223g (2.06mol), chlorobenzene 464g (4.12mol), potassium hydroxide 166.6g (2.68mol ) and cuprous chloride 3g, reflux dehydration and condensation reaction at 180°C for 5 hours, cool down to below 110°C, filter, wash the filter residue with chlorobenzene until it is colorless, wash the filtrate with 10% dilute sulfuric acid (200mL), separate layers, and the organic layer Distilled under reduced pressure to collect m-phenoxytoluene 323g, yield 85%, gas phase content GC=99% (ie purity).

[0048] (2) Preparation of m-phenoxybenzaldehyde: Add 970mL of sulfuric acid of 55% concentration and 323g (1.75mol) of m-phenoxytoluene to a 2000mL four-necked bottle, heat to 80°C, add manganese trioxide 277.6g in batches ( 1.75mol), after adding and keeping warm for 3 hours, the ...

Embodiment 2

[0054] (1) Preparation of m-phenoxytoluene: 2000mL four-necked bottle is equipped with stirring, thermometer and water separator, add m-cresol 223g (2.06mol), bromobenzene 646g (4.12mol), potassium hydroxide 166.6g (2.68mol ) and cuprous chloride 3g, reflux dehydration and condensation reaction at 180°C for 5 hours, cool down to below 110°C, filter, wash the filter residue with chlorobenzene until it is colorless, wash the filtrate with 10% dilute sulfuric acid (200mL), separate layers, and the organic layer Distilled under reduced pressure, collected m-phenoxytoluene 320g, yield 84.3%, gas phase content GC=99%

[0055] (2) Preparation of m-phenoxybenzaldehyde: Add 970mL of sulfuric acid of 55% concentration and 320g (1.74mol) of m-phenoxytoluene to a 2000mL four-necked bottle, heat to 80°C, add 277.0g of manganese trioxide in batches ( 1.75mol), after adding and keeping warm for 3 hours, the liquid phase detection raw material <0.5% stopped the reaction, filtered while it was...

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Abstract

The invention provides a preparation method of m-phenoxy benzaldehyde, and belongs to the technical field of synthesis of medical intermediates. The preparation method comprises the following steps: mixing m-cresol, halogenated benzene, inorganic base and a catalyst for condensation reaction to obtain m-phenoxy toluene; mixing the m-phenoxy toluene with an oxidant, and carrying out an oxidation reaction under acidic conditions to obtain m-phenoxy benzaldehyde. According to the preparation method, m-cresol and halogenated benzene are taken as raw materials, the cost of the raw materials is low, m-phenoxy toluene is firstly prepared through a condensation reaction, then m-phenoxy toluene is oxidized into m-phenoxy benzaldehyde, the yield of the product is high, and the preparation is simple. The result of the embodiment shows that the yield of the m-phenoxybenzaldehyde prepared by the method is 56.8% or above.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of m-phenoxybenzaldehyde. Background technique [0002] m-phenoxybenzaldehyde, also known as 3-methoxybenzaldehyde, 3-formyl diphenyl ether, referred to as ether aldehyde, is an important intermediate for the synthesis of a series of high-efficiency, broad-spectrum, safe and low-toxic pyrethroid pesticides Body, is light yellow liquid, insoluble in water, soluble in organic solvents such as alcohol, benzene, the synthetic method of m-phenoxybenzaldehyde of current report has following several: [0003] (1) Take benzaldehyde as raw material, react with bromine to obtain m-bromobenzaldehyde, then condense with sodium phenoxide to obtain product m-phenoxybenzaldehyde. A small amount of p-bromobenzaldehyde is generated when the first step of this method is substituted, and m-bromobenzaldehyde is prone to disproportionation under...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/36C07C47/575
Inventor 王栋伟赵宏洋王诚刘涛
Owner 锦州三丰科技有限公司