Method for preparing p-hydroxyphenyl ethanol

A technology for p-hydroxyphenethyl alcohol and methyl p-hydroxyphenylacetate, which is applied in the field of compound preparation, can solve the problems of expensive amount of reducing agent, difficulty in realizing industrialization, and high requirements for reaction conditions, achieves that the amount of catalyst can be reused, and is beneficial to the environment Protection, the effect of less catalyst dosage

Inactive Publication Date: 2013-08-07
XIAMEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method disclosed in Chinese patent CN101225023A proposes to use ethyl p-hydroxyphenylacetate as a raw material, and obtain the corresponding alcohol by reducing the ester with lithium aluminum hydride or sodium borohydride at a low temperature, and the yield is 72%, but there are reducing agents that are relatively expensive and used in large quantities. shortcoming
The method disclosed in Chinese patent CN100432035C uses phenol and acetic anhydride as raw materials

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0011] Example 1

[0012] In a 100ml autoclave with a stirring device, dissolve 20.0g methyl p-hydroxyphenylacetate in 40.0ml methanol, and add 2g reduced CuO-ZnO-Al 2 O 3 For the catalyst, nitrogen is introduced to remove the air in the autoclave three times, and then hydrogen is introduced for replacement three times. The reaction pressure is 5.0MPa and the reaction temperature is 220°C for 24h. The reaction solution was collected, and the product was detected by high performance liquid chromatography. The chromatographic column was a C18 column, an ultraviolet detector, the ultraviolet detection wavelength was 277 nm, and the column temperature was 25°C. The yield of p-hydroxyphenethyl alcohol was 50.2%.

[0013] Product purification: the reaction solution was spin-dried under reduced pressure, and the solvent methanol was recovered to obtain a white solid. It was recrystallized with chloroform to obtain colorless needle-like crystals. The precipitated crystals are filtered o...

Example Embodiment

[0014] Example 2

[0015] The preparation method, detection method and purification method of p-hydroxyphenethyl alcohol are the same as in Example 1, but the reaction pressure in the autoclave during the reaction is 7.5 MPa, and the reaction time is 8 h. Other conditions remain unchanged, and the yield of p-hydroxyphenylethanol is 82.4%.

Example Embodiment

[0016] Example 3

[0017] The preparation method, detection method and purification method of p-hydroxyphenethyl alcohol are the same as in Example 1, but the reaction pressure in the autoclave is 10.0 MPa during the reaction, but the reaction time is 2 h. Other conditions remain unchanged, and the yield of p-hydroxyphenethyl alcohol is 40.7%.

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PUM

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Abstract

The invention provides a method for preparing p-hydroxyphenyl ethanol, relating to a preparation method of a compound. The method for preparing the p-hydroxyphenyl ethanol, provided by the invention, has the advantages of simplicity in operation, environmental friendliness, high yield, reusable catalyst and applicability to industrial production. The method comprises the steps of: putting p-hydroxyphenyl acetate serving as a raw material, a copper-based catalyst serving as a hydrogenation catalyst, and a reaction solvent in a reaction vessel, replacing air in the reaction vessel with nitrogen gas and hydrogen gas respectively, and then, reacting; and carrying out depressurized spin drying on a solution after reacting, recovering the reaction solvent so as to obtain white solids, recrystallizing by using chloroform so as to obtain colorless needle-like crystals, filtering out precipitated crystals, washing filter cakes with water, and then, carrying out vacuum drying, thereby obtaining the p-hydroxyphenyl ethanol. The copper-based catalyst is used, so that the catalyst is little in consumption and can be reused; used solvents can be all recovered, so that the environmental protection and cost reduction are benefited; and the yield of the p-hydroxyphenyl ethanol is high and can reach over 80% at highest.

Description

Technical field [0001] The invention relates to a method for preparing a compound, in particular to a method for preparing p-hydroxyphenethyl alcohol by catalytic hydrogenation of p-hydroxyphenylacetate. Background technique [0002] P-Hydroxyphenethyl alcohol (also known as β-p-hydroxyphenethyl alcohol, tyrosol) is an important pharmaceutical and perfume intermediate, which can synthesize many useful drugs, such as betaolol, which is used to treat open-angle epioptic eye , Salidroside for the treatment of lung heat, cough and blast, and metoprolol for the treatment of hypertension and myocardial infarction. [0003] The methods for synthesizing p-hydroxyphenethyl alcohol include fermentation, 4-substituted phenol derivatives as raw materials, synthetic methods with aldehydes as intermediates, phenethylamine synthesis, phenethyl alcohol synthesis, and 4-substituted nitrosamine Base benzene is a raw material synthesis method and ester reduction method. The method disclosed in Chin...

Claims

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Application Information

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IPC IPC(8): C07C37/56C07C39/11
Inventor 伊晓东吴钟芳宋文静方维平万惠霖王德峰朱小飞
Owner XIAMEN UNIV
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