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Preparation method of hydroquinone derivative

A technology of hydroquinone and derivatives, which is applied in the field of new preparation of pharmaceutical intermediates, and can solve the problems of high cost, sea urchin resources, unfavorable printing and dyeing industry, etc.

Inactive Publication Date: 2018-03-09
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditionally, people extract Ethylspinazarin from the remaining sea urchin shells (including thorns) after taking out sea urchin eggs. The production efficiency is low, it needs to consume a lot of sea urchin resources, and the cost is high, which is not conducive to wide application in the printing and dyeing industry.

Method used

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  • Preparation method of hydroquinone derivative
  • Preparation method of hydroquinone derivative
  • Preparation method of hydroquinone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Preparation of Compound 2

[0026] Add 50g of hydroquinone to 250ml of acetyl chloride, stir overnight at room temperature, concentrate under reduced pressure to remove the remaining acetyl chloride, then add saturated aqueous sodium bicarbonate and ethyl acetate for extraction, separate, dry, and concentrate to obtain 61g of compound 2.

[0027] (2) Preparation of Compound 3

[0028] Add 60g of compound 2 into 550ml of dichloromethane, then add 27g of zinc chloride, heat and reflux and stir for 16 hours, cool to room temperature, slowly pour the reaction solution into water, extract and separate, collect the organic phase, separate, dry, After concentration, the residue was separated on a silica gel column to obtain 21 g of compound 3.

[0029] (3) Preparation of 3-bromo-2,5-diacetylhydroquinone

[0030] Add 20g of compound 3 to 200ml of carbon disulfide, add 8.5g of anhydrous aluminum trichloride, then add 28ml of acetyl chloride, heat and reflux and stir for 1...

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PUM

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Abstract

The invention discloses a preparation method of a hydroquinone derivative 3-bromo-2,5-diacetylhydroquinone. With 2-bromohydroquinone as a start raw material, the target compound is prepared by acylation, rearrangement and Friedel-Crafts reaction, wherein the compound is an important intermediate for preparing natural pigment.

Description

technical field [0001] The invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to a preparation process of a hydroquinone derivative 3-bromo-2,5-diacetyl hydroquinone. technical background [0002] Hydroquinone derivative 3-bromo-2,5-diacetylhydroquinone, the structural formula is: [0003] [0004] The compound is an intermediate derivative for preparing the natural product ethylspinazarin. Ethylspinazarin is a sea urchin extract, which is a high-grade natural pigment. Traditionally, people extract Ethylspinazarin from the remaining sea urchin shells (including thorns) after taking out sea urchin eggs. The production efficiency is low, it needs to consume a large amount of sea urchin resources, and the cost is high, which is not conducive to wide application in the printing and dyeing industry. [0005] Dyes and pigments are widely used in textiles, food, light industry, coatings, inks and other fields, and are closely relate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/46C07C49/825
CPCC07C67/14C07C45/46C07C45/54C07C69/16C07C49/825
Inventor 不公告发明人
Owner 湖南华腾制药有限公司
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