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Method for preparing 2-( methoxyl-methyl) phenyl-1,4-diamine

A technology of methoxymethyl and phenyl, which is applied in the field of preparation of 1,4-diphenylamine, can solve the problems of being unsuitable for industrial production, unsuitable for industrial production, expensive reducing agent, etc., and achieve simplified operation and convenient operation , the effect of less waste

Active Publication Date: 2015-07-01
ZHEJIANG DINGLONG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0026] This method uses sodium borohydride or lithium aluminum tetrahydrogen as reducing agent, which has certain potential safety hazards, and these reducing agents are expensive and costly to produce, so they are not suitable for industrial production
[0027] Based on the above, there are certain problems in the current synthesis route of 2-methoxymethyl-1,4-diphenylamine, which is not suitable for industrial production

Method used

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  • Method for preparing 2-( methoxyl-methyl) phenyl-1,4-diamine
  • Method for preparing 2-( methoxyl-methyl) phenyl-1,4-diamine
  • Method for preparing 2-( methoxyl-methyl) phenyl-1,4-diamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Preparation of o-nitrobenzyl methyl ether:

[0067] At room temperature, add 275g ethyl acetate, 45.9g 0.3mol o-nitrobenzyl alcohol, 38.2g 0.36mol sodium carbonate to a 1000ml four-neck flask, stir for 10min, and slowly add 40.5g 0.45mol carbonic acid dropwise at 20-25°C Dimethyl ester, the dropping time is 1.0h, keep warm at 50~60°C for 0.5h~1.0h after dropping, HPLC central control, stop the reaction when the raw material is less than 1.0%, drop to room temperature, add 100ml of water, continue to stir for 20min , standing still for liquid separation, extracting the aqueous phase with 100ml ethyl acetate, standing to separate layers, combining the organic phases, and distilling under reduced pressure to recover ethyl acetate to obtain a yellow solid, which was blown and dried overnight at 30°C to obtain o-nitrobenzyl Methyl ether: 47.4g, yield: 94.6%, HPLC: 98.5%.

[0068] Preparation of o-aminobenzyl methyl ether:

[0069] At room temperature, add 140.0g of 0.833mo...

Embodiment 2

[0077] Preparation of o-nitrobenzyl methyl ether:

[0078] At room temperature, add 280g of acetonitrile, 45.9g of 0.3mol o-nitrobenzyl alcohol, 38.2g of 0.36mol sodium carbonate into a 1000ml four-necked flask, stir for 10min, and slowly add 40.5g of 0.45mol dimethyl carbonate dropwise at 20-25°C Ester, the dropping time is 1.0h, keep warm at 55~65°C for 0.5h~1.0h after dropping, HPLC central control, stop the reaction when the raw material is less than 1.0%, drop to room temperature, add 100ml of water, continue to stir for 20min, static Separate the liquid, extract the aqueous phase with 100ml ethyl acetate, let stand to separate the layers, combine the organic phases, and distill under reduced pressure to recover the ethyl acetate to obtain a yellow solid, which is blown and dried overnight at 30°C to obtain o-nitrobenzyl methyl ether : 48.3g, yield: 96.4%, HPLC: 98.7%.

[0079] Preparation of o-aminobenzyl methyl ether:

[0080]At room temperature, add 140.0g of 0.833mo...

Embodiment 3

[0088] Preparation of o-nitrobenzyl methyl ether:

[0089] At room temperature, add 280g of acetonitrile, 45.9g of 0.3mol o-nitrobenzyl alcohol, 38.2g of 0.36mol sodium carbonate into a 1000ml four-neck flask, stir for 10min, and slowly add 56.7g of 0.45mol dimethyl sulfate dropwise at 15-25°C Ester, the dropping time is 1.0h, keep warm at 50~60°C for 0.5h~1.0h after dropping, HPLC central control, stop the reaction when the raw material is less than 1.0%, drop to room temperature, add 100ml of water, continue stirring for 20min, static Separate the liquid, extract the aqueous phase with 100ml ethyl acetate, let stand to separate the layers, combine the organic phases, and distill under reduced pressure to recover the ethyl acetate to obtain a yellow solid, which is blown and dried overnight at 30°C to obtain o-nitrobenzyl methyl ether : 47.9g, yield: 95.6%, HPLC: 98.0%.

[0090] Preparation of o-aminobenzyl methyl ether:

[0091] At room temperature, add 140.0g of 0.833mol ...

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Abstract

The invention relates to a method for preparing 2-(methoxyl-methyl) phenyl-1,4-diamine. The method comprises the following steps: by taking o-nitrobenzyl alcohol as a raw material, performing methylation and hydrogenation reduction reaction so as to obtain 2-(methoxyl methyl) aniline, performing azo reaction on 2-( methoxyl methyl) aniline by taking an aniline substance as a coupling agent so as to obtain 2-(methoxyl methyl)-5-azo aniline, performing hydrogenolysis reaction on 2-(methoxyl methyl)-5-azo aniline in the presence of a hydrogenation catalyst so as to generate 2-(methoxyl methyl) phenyl-1,4-diamine and a corresponding coupling agent, separating and purifying, thereby respectively obtaining 2-(methoxyl methyl) phenyl-1,4-diamine and a corresponding coupling agent. The method has the characteristics that the atom economy property is good, a small amount of the tree wastes can be generated, the raw materials are cheap, auxiliary materials can be recycled and reused, the aspects such as operation simplification, pollution reduction and economic benefit increase are remarkably improved, and the method is applicable to industrial production.

Description

technical field [0001] The invention relates to a preparation method of 2-substituted 1,4-diphenylamine, especially a preparation method of 2-(methoxymethyl)phenyl-1,4-diamine. Background technique [0002] 2-Substituted-1,4-diphenylamines and their physiologically compatible salts can be used as main intermediates in oxidative hair coloration. For example, 2-methoxymethyl-1,4-diphenylamine and its physiologically compatible salts can be used as main intermediates in oxidative hair coloring, and have great market potential. The main methods of oxymethyl-1,4-phenylenediamine are as follows: [0003] Method 1 (Patent No.: CN103124718A): The process route is shown in Formula 1: [0004] [0005] Formula 1 [0006] The method has long reaction steps, low yield, and produces more three wastes, and is not suitable for industrialized production. [0007] Method 2 (Patent No.: CN 103124718): The process route is shown in Formula 2: [0008] [0009] Formula 2 [0010] Th...

Claims

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Application Information

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IPC IPC(8): C07C217/76C07C213/02C07C213/10
Inventor 金宁人秦振伟潘志军施云龙朱炯顾峰雷
Owner ZHEJIANG DINGLONG TECH
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