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Method for synthesizing tyrosol

A technique for the synthesis of p-hydroxyphenylethanol and its synthesis method, which is applied in the field of synthesis of pharmaceutical intermediate p-hydroxyphenylethanol, can solve the problems of high anhydrous requirements, difficult separation, low yield, etc., and achieve environmental protection, low price, cost reduction effect

Inactive Publication Date: 2008-07-23
NANJING RALLY BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the existence of ortho and para products in the first step of nitration reaction, it is difficult to separate, and there are many reaction steps.
[0006] 2. With p-hydroxyphenyl acetate as raw material, metal hydride: lithium aluminum tetrahydrogen is used as a reducing agent to reduce carboxylate to alcoholic hydroxyl groups, but lithium aluminum tetrahydrogen is expensive, which restricts the method in industrial production Applications
[0007] 3. Using p-hydroxyphenyl acetate as raw material and sodium metal / sodium ethoxide as reducing agent, p-hydroxyphenylethyl alcohol can also be obtained, but the yield is low and the anhydrous requirement is high

Method used

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  • Method for synthesizing tyrosol

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Experimental program
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Effect test

Embodiment 1

[0020] (1) At 0°C, put 120ml (103g) of ethylene glycol dimethyl ether and 60g (0.36mol) of methyl p-hydroxyphenylacetate into the reactor, and stir for 15 minutes to completely dissolve the methyl p-hydroxyphenylacetate in ether.

[0021] (2) Add 15.2 g (0.4 mol) of sodium borohydride, gas is released, stir for 15 minutes, and keep at 0-10°C.

[0022] (3) At 0°C, add 80 ml of boron trifluoride diethyl ether dropwise, and the drop is completed in about 30 minutes. Continue stirring for 2 hours, add 300 ml of water, and stir for 30 minutes.

[0023] (4) After the reaction is completed, ethylene glycol dimethyl ether is recovered under reduced pressure. After adding 100ml of water, a large amount of white solids precipitated, and stirred for 15 to 20 minutes. Filter and wash the filter cake with ice water to obtain the product. Vacuum-dried to obtain 37 g of dry product, content (HPLC) ≥ 98.8%, mp: 88-92°C, yield 74.3%.

Embodiment 2

[0025] (1) At 0°C, put 120ml (103g) of ethylene glycol dimethyl ether and 64.8g (0.36mol) of ethyl p-hydroxyphenylacetate into the reactor, and stir for 15 minutes to completely dissolve the ethyl p-hydroxyphenylacetate in ether.

[0026] (2) Add 15.2 g (0.4 mol) of sodium borohydride, gas is released, stir for 15 minutes, and keep at 0-10°C.

[0027] (3) At 0°C, add 80 g of aluminum trichloride and finish adding in about 30 minutes, continue stirring for 2 hours, add 300 ml of water, and stir for 30 minutes.

[0028] (4) After the reaction is completed, ethylene glycol dimethyl ether is recovered under reduced pressure. After adding 200ml of water, a large amount of white solids were precipitated, and stirred for 15 to 20 minutes. Filter and wash the filter cake with ice water to obtain the product. Vacuum-dried to obtain 36 g of dry product, content (HPLC) ≥ 98.5%, mp: 88-92°C, yield 72.4%.

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Abstract

The invention relates to a synthesis method of 4-hydroxyphenethyl alcohol, which is characterized in that: ethyl-hydroxybenzoate is used as starting raw material and sodium borohydride (or potassium borohydride) is used as reducing agent and aluminium chloride or boron trifluoride diethyl etherate is used as catalyst for reduction reaction in proper solvent, thereby getting 4-hydroxyphenethyl alcohol. The synthesis method of 4-hydroxyphenethyl alcohol has the advantages of industrial production for the 4-hydroxyphenethyl alcohol, lower cost and feasible operation. The yield can reach 72%.

Description

technical field [0001] The invention relates to the field of organic chemical industry, in particular to a method for synthesizing a pharmaceutical intermediate p-hydroxyphenethyl alcohol. Background technique [0002] P-Hydroxyphenylethanol, also known as salidroside aglycone, is a pharmaceutical intermediate, scientific name: P-Hydroxyphenylethanol (P-Hydroxyphenylethanol), and its structural formula is as follows: [0003] [0004] There are roughly three types of methods for synthesizing p-hydroxyl in the past: [0005] 1. Using phenylethyl alcohol as a raw material, carry out nitration, reduction, and heavy hydrogenation, and convert the deuterium salt into alcoholic hydroxyl in ethanol to obtain p-hydroxyphenylethyl alcohol. However, due to the existence of ortho and para products in the first step of nitration reaction, it is difficult to separate, and there are many reaction steps. [0006] 2. With p-hydroxyphenyl acetate as raw material, metal hydride: lithium ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/00C07C39/11
Inventor 陈新高相森梅以成
Owner NANJING RALLY BIOCHEM
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