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Method for synthesizing 4-alkylresorcinol through solvent-free system

A technology of alkyl resorcinol and acyl resorcinol, which is applied in the field of solvent-free synthesis of 4-alkylresorcinol, can solve problems such as unfavorable environmental protection, achieve waste reduction, mild reaction conditions, and reduce environmental protection cost effect

Active Publication Date: 2019-03-29
上海贤鼎生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to overcome the problem that the traditional synthesis process of 4-alkylresorcinol depends on the organic solvent system and is not conducive to environmental protection, the present invention provides a method for synthesizing 4-alkylresorcinol in a solvent-free system. The triethylsilane / trifluoroacetic acid system is applied to the synthesis of 4-alkylresorcinol, the reaction conditions are milder, and the post-treatment method is simple; and because there is no solvent in the system, the waste generated during industrial scale-up is also greatly reduced. Make the whole process greener

Method used

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  • Method for synthesizing 4-alkylresorcinol through solvent-free system
  • Method for synthesizing 4-alkylresorcinol through solvent-free system
  • Method for synthesizing 4-alkylresorcinol through solvent-free system

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Experimental program
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Effect test

Embodiment 1

[0030] (1) Dissolve raw materials resorcinol (500g, 4.54mol) and zinc chloride (804g, 5.9mol) in n-butyric acid (600g, 6.81mol), heat to 100°C and stir. After the reaction of the raw materials is complete, the reaction solution is cooled and added to water. After stirring, a large amount of solids are precipitated, filtered and washed with water. After the solids are dried, recrystallized to obtain 4-n-butyryl resorcinol (724g, figure 1 , HPLC: 98.3%);

[0031] (2) Dissolve 4-n-butyryl resorcinol (724g, 4.02mol) in trifluoroacetic acid (2.29kg, 20.1mol), cool in an ice-water bath to 0°C, add triethylsilane (1.4kg, 12.06mol), after the addition, the reaction solution was heated to 60°C and stirred overnight. After the reaction of the raw materials is complete, the reaction solution is poured into water to quench, and after continuous stirring, the layers are separated, the organic layer is extracted with ethyl acetate, the combined organic phase is washed with saturated brine,...

Embodiment 2

[0033] (1) The raw material resorcinol (500g, 4.54mol) and zinc chloride (618g, 4.54mol) were dissolved in n-butyric acid (400g, 4.54mol), heated to 80°C and stirred. After the reaction of the raw materials was complete, the reaction solution was cooled and added to water. After stirring, a large amount of solids were precipitated, filtered and washed with water. The obtained solids were dried and recrystallized to obtain 4-n-butyryl resorcinol (561 g);

[0034] (2) Dissolve 4-n-butyryl resorcinol (561g, 3.1mol) in trifluoroacetic acid (707g, 6.2mol), cool in an ice-water bath to 0°C, add triethylsilane (721g, 6.2mol) dropwise ), after the addition, the reaction solution was heated to 40°C and stirred overnight. After the reaction of the raw materials is complete, the reaction solution is poured into water to quench, and after continuous stirring, the layers are separated, the organic layer is extracted with ethyl acetate, the combined organic phase is washed with saturated br...

Embodiment 3

[0036](1) The raw material resorcinol (500g, 4.54mol) and zinc chloride (1.24kg, 9.08mol) were dissolved in n-butyric acid (800g, 9.08mol), heated to 120°C and stirred. After the reaction of the raw materials was complete, the reaction solution was cooled and added to water. After stirring, a large amount of solids were precipitated, filtered and washed with water. The obtained solids were dried and recrystallized to obtain 4-n-butyryl resorcinol (602 g);

[0037] (2) Dissolve 4-n-butyryl resorcinol (602g, 3.34mol) in trifluoroacetic acid (3.81kg, 33.4mol), cool in an ice-water bath to 0°C, add triethylsilane (1.94kg, 16.7mol), after the addition, the reaction solution was heated to 80°C and stirred overnight. After the reaction of the raw materials is complete, the reaction solution is poured into water to quench, and after continuous stirring, the layers are separated, the organic layer is extracted with ethyl acetate, the combined organic phase is washed with saturated brin...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 4-alkylresorcinol through a solvent-free system. The method comprises the following stepsthat (1) resorcinol, zinc chloride and alkyl acid are evenly mixed, heated and stirred for a reaction, after cooling, water is added to precipitate a solid, filtering, drying and recrystallization areconducted, and thus 4-acylresorcinol is obtained; (2) the 4-acylresorcinol is dissolved into trifluoroacetic acid, triethyl silicane is added dropwise, heating and stirring are conducted for a reaction, cooling and standing are conducted for layering, an organic layer is extracted and dried, filtration and concentration are conducted to obtain a crude product, recrystallization is conducted, andthe 4-alkylresorcinol is obtained. According to the method, a triethyl silicane / trifluoroacetic acid system is applied to synthesis of the 4-alkylresorcinol for the first time, the reaction conditionis gentler and easier to control, and a post-treatment method is simple; and the system does not contain a solvent, water materials generated during industrial amplification are also greatly reduced,and thus the whole process is more environment friendly.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 4-alkyl resorcinols in a solvent-free system. Background technique [0002] Alkyl resorcinol is a kind of widely used chemical intermediates. It is used as anti-corrosion agent, bactericide, epoxy resin and some polymer components in industry; it is used as medicine and Food preservatives, and hair styling and skin depigmentation in the field of beauty and skin care. In recent years, 4-alkylresorcinol has been found to have a good inhibitory effect on tyrosinase, thereby effectively controlling the production and deposition of melanin in the skin, and producing an obvious brightening and whitening effect on the skin. Its market demand The increase is particularly pronounced in Asia. [0003] At present, the synthesis of 4-alkylresorcinol in industry is mainly obtained through two-step reactions: the first step is to use resorcinol as raw mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/08C07C37/00C07C49/825C07C45/45
CPCC07C37/002C07C45/455C07C49/825C07C39/08
Inventor 何皓蒋昌盛董海平
Owner 上海贤鼎生物科技有限公司
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