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O-mercapto phenol derivatives and preparation method thereof

A technology of ortho-mercaptophenol derivatives, which is applied in the field of preparation of ortho-mercaptophenol derivatives, can solve the problems of low yield, high cost, and few researches on preparation methods of mercaptophenol derivatives, and achieve broad application prospects , complex and diverse effects

Active Publication Date: 2014-07-02
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0024] In summary, the prior art basically studies the method for preparing mercaptophenol, which has the disadvantages of low yield and high cost, but there are few studies on the preparation method of mercaptophenol derivatives.

Method used

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  • O-mercapto phenol derivatives and preparation method thereof
  • O-mercapto phenol derivatives and preparation method thereof
  • O-mercapto phenol derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] A kind of ortho mercaptophenol derivative, its structure is as follows:

[0063]

[0064] A kind of above-mentioned ortho mercaptophenol derivative, its preparation method comprises the following steps:

[0065] a. Precursor compound synthesis:

[0066] (1) Using sodium hydride (400mmol) as a catalyst, dimethyl malonate (200mmol) and propargyl bromide (440mmol) were added to anhydrous acetonitrile and stirred in an ice-water bath for 8 hours, and the reaction product was washed with water and used Extracted with ethyl acetate, spin-dried under reduced pressure, column chromatography (volume ratio ethyl acetate:petroleum ether=1:100) to obtain a white solid product, wherein the molar ratio of dimethyl malonate to propargyl bromide was 1:2.2 .

[0067] (2) The white solid product (80mmol) was mixed with phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 : In the anhydrous and oxygen-free catalytic system of CuI=(3:1), triethylamine is used as a base, anhydrous acetonitril...

Embodiment 2

[0077] A kind of ortho mercaptophenol derivative, its structure is as follows:

[0078]

[0079] A kind of above-mentioned ortho mercaptophenol derivative, its preparation method comprises the following steps:

[0080] a. Precursor compound synthesis:

[0081] (1) Using sodium hydride (400mmol) as a catalyst, diethyl malonate (200mmol) and propargyl bromide (440mmol) were added to anhydrous acetonitrile and stirred in an ice-water bath for 8 hours, and the reaction product was washed with water and used Extracted with ethyl acetate, spin-dried under reduced pressure, column chromatography (volume ratio ethyl acetate:petroleum ether=1:100) to obtain a white solid product, wherein the molar ratio of diethyl malonate to propargyl bromide was 1:2.2 ;

[0082] (2) The white solid product (80mmol) was mixed with phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 : In the anhydrous and oxygen-free catalytic system of CuI (3:1), with triethylamine as base, with anhydrous acetonitrile ...

Embodiment 3

[0092] A kind of ortho mercaptophenol derivative, its structure is as follows:

[0093]

[0094] A kind of above-mentioned ortho mercaptophenol derivative, its preparation method comprises the following steps:

[0095] a. Precursor compound synthesis:

[0096] (1) Using sodium hydride (400mmol) as a catalyst, dipropyl malonate (200mmol) and propargyl bromide (440mmol) were added to anhydrous acetonitrile and stirred in an ice-water bath for 8 hours, and the reaction product was washed with water and used Extracted with ethyl acetate, spin-dried under reduced pressure, column chromatography (volume ratio ethyl acetate:petroleum ether=1:100) to obtain a white solid product, wherein the molar ratio of dipropyl malonate to propargyl bromide was 1:2.2 .

[0097] (2) The white solid product (80mmol) was mixed with phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 : In the anhydrous and oxygen-free catalytic system of CuI (3:1), with triethylamine as base, with anhydrous acetonitril...

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Abstract

The invention provides o-mercapto phenol derivatives and a preparation method thereof. The preparation method comprises the following steps: a, synthesizing a precursor; b, synthesizing a target product; and c, purifying. Compared with the prior art, the invention provides a brand new synthetic method of poly-substituted o-mercapto phenol for generating a series of novel o-mercapto phenol derivatives. Compared with common o-mercapto phenol derivatives, the o-mercapto phenol derivatives prepared by the method provided by the invention have multiple rings, so that the o-mercapto phenol derivatives are more complex and diverse in structure and further show a broader application prospect in chemical industry production and clinical medicines.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of ortho-mercaptophenol derivatives. Background technique [0002] Ortho-mercaptophenol and its derivatives are widely used in industrial production and scientific research. For example, mercaptophenol is mainly used in medicine, pesticides, polymer materials and organic synthesis auxiliaries, and is also used in the preparation of local anesthetics. In view of the special importance of ortho-mercaptophenol and its derivatives, how to expand the synthetic route of mercaptophenol and its derivatives has aroused the active thinking of countless organic synthesizers and chemists, and came up with some very effective methods. [0003] Common synthetic routes of mercaptophenols can be divided into the following five categories: [0004] 1. Chlorosulfonic acid method [0005] This method uses benzene as a raw material, and it is prepared by chlorosulfonation, iro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/62C07C319/14
Inventor 胡益民尹飞
Owner ANHUI NORMAL UNIV
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