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The method for one-pot synthesis of m-aminophenethyl ether

A technology of aminophenetole and m-aminophenol, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxyl compounds, etc., can solve the problems of increased cost, difficult recovery of phase transfer catalysts, and many wastes in the reduction process, and achieves Less pollution, fewer reaction steps, avoiding the effects of by-products

Active Publication Date: 2018-05-11
ZHEJIANG HONGSHENG CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has used the more expensive triethylbenzyl ammonium chloride, triethylbenzyl ammonium bromide phase transfer catalyst, phase transfer catalyst is difficult to reclaim and has increased cost, adopts Na simultaneously 2 There are more three wastes in the S reduction process

Method used

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  • The method for one-pot synthesis of m-aminophenethyl ether
  • The method for one-pot synthesis of m-aminophenethyl ether
  • The method for one-pot synthesis of m-aminophenethyl ether

Examples

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Effect test

Embodiment 1

[0032] Embodiment 1, a kind of preparation method of m-aminophenetole (the method for synthesizing m-aminophenetole in one pot), take m-aminophenol as raw material, carry out the following steps successively:

[0033] (1) Put 21.8g (0.20mol) of m-aminophenol, 8.0g (0.20mol) of sodium hydroxide, and 120mL of solvent (N,N-dimethylformamide) into a 250mL reactor, and then add 0.79g (0.010mol , 5% of the molar amount of m-aminophenol) pyridine and 16.77 g (0.220 mol) ethyl chloride. After the addition, the reaction kettle was sealed and stirred at room temperature for 0.5h. Then raise the temperature to 50°C and react for 2 hours. After the reaction, cool the reaction solution to room temperature, filter the reaction solution, and keep the filtrate for use;

[0034] (2) The filtrate of step (1) gained is distilled under reduced pressure under 11mmHg vacuum degree, collects respectively the solvent of 40~55 ℃ fraction and 25.8g of light yellow oily liquid of 116~135 ℃ fraction, yi...

Embodiment 12～ Embodiment 18

[0040] Change the name of the catalyst in Example 1, the name of the base, and the molar weight remain unchanged; the rest are the same as in Example 1, and Example 12 to Example 18 are obtained respectively. The yield and purity of gained m-aminophenetole are shown in Table 2.

[0041] Table 2

[0042]

Embodiment 19

[0043] Example 19. The solvent in Example 1 was changed from N,N-dimethylformamide to dimethyl sulfoxide, and the dosage remained unchanged; the rest were the same as in Example 1. The yield is 94.1%; m-aminophenetole: N-ethyl m-aminophenetole: N-ethyl m-aminophenol (O:NO:N)=99.0%:1.0%:0.

[0044] Comparative Example 1-1. In Example 1, "under stirring at room temperature for 0.5h" was deleted, and then "reaction at 50°C for 2h" was changed to "reaction at 50°C for 2.5h", and the rest was the same as in Example 1. The yield is 63.4%; m-aminophenetole: N-ethyl m-aminophenetole: N-ethyl m-aminophenol (O:NO:N)=87.5%:12.5%:0.

[0045] Comparative example 1-2, change the time of stirring at normal temperature in Example 1 from 0.5h to 2h; the rest is the same as Example 1. The yield is 94.1%; m-aminophenetole: N-ethyl m-aminophenetole: N-ethyl m-aminophenol (O:NO:N)=99.0%:1.0%:0.

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Abstract

The invention discloses a synthesis method of m-phenetidine by a one-pot reaction. The method comprises the following steps: m-aminophenol, alkali and a solvent are thrown into a reaction vessel, and then only an alkylating agent or a catalyst and an alkylating agent are added at the same time, after materials are added, the reaction vessel is enclosed, and stirring is carried out for 0.5-1 hour at room temperature; the temperature is raised to 40-80 DEG C, a reaction is carried out for 1-8 hours, after the reaction, obtained reaction solution is cooled to room temperature and filtered, and filtrate is obtained; reduced pressure distillation for the filtrate is carried out, and m-phenetidine is obtained. The synthesis method of m-phenetidine has the characteristics of low reaction temperature, high safety performance, convenient operation, high purity and high yield of the product, etc.

Description

technical field [0001] The invention relates to a synthesis method of m-aminophenetole. Background technique [0002] m-Aminophenetole, whose molecular formula is C 8 h 11 NO, its structural formula is as follows: [0003] [0004] The pure product of m-aminophenethyl ether is a colorless oily liquid, which is an important intermediate for dyes and other organic synthesis. [0005] The method of the synthetic m-aminophenethyl ether of present report mainly contains following several kinds: [0006] Method 1, with m-aminophenol as starting raw material, in order to avoid -NH 2 Alkylation uses acetic acid acetylation to protect the amino group, after alkylation with bromoethane, hydrochloric acid hydrolysis to deacetylate, and alkali neutralization, it is currently the main industrial production method. The method has many process steps and complicated operation; hydrolysis with hydrochloric acid requires higher equipment, and waste water pollutes the environment more;...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/06C07C217/84
CPCC07C213/06C07C217/84
Inventor 孔明贡晗陶建国彭文博万德贵
Owner ZHEJIANG HONGSHENG CHEM IND
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