Synthesis method of 3-(4-hydroxyphenyl)propanamide

A synthetic method, the technology of hydroxyphenyl, applied in the field of synthesis of 3-propanamide, can solve the problems of troublesome handling, high price, unsuitable for mass production, etc., and achieve cost reduction, convenient post-processing, and omission of catalysts and raw materials Effect

Inactive Publication Date: 2014-09-10
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The first step uses p-nitrophenol and DCC, not only the cost is high, but also the post-processing of DCC is troublesome
[0006] The methanol solution of ammonia is used in the second step, which is expensive, and the final product needs to be purified by column chromatography, the efficiency is low, and the yield is about 75%, which is not suitable for mass production

Method used

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  • Synthesis method of 3-(4-hydroxyphenyl)propanamide
  • Synthesis method of 3-(4-hydroxyphenyl)propanamide
  • Synthesis method of 3-(4-hydroxyphenyl)propanamide

Examples

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Embodiment 1

[0024] The synthesis of embodiment 13-(4-hydroxyphenyl) propanamide

[0025] Add 15mL of thionyl chloride to 2g of p-hydroxyphenylpropionamide, stir until clear, take a sample, add a small amount of methanol, PE:EA=5:1 spot plate, about 1-1.5h.

[0026] Then spin off the thionyl chloride, add a small amount of acetonitrile to dissolve, slowly add dropwise to 20mL of 25-28% ammonia water at 0°C, stir for 15-30min, sample, acidify, DCM:MeOH=10:1 plate.

[0027] After the reaction is completed, spin off the solvent, add a small amount of concentrated hydrochloric acid to the obtained solid, the solid turns from yellow to white, spin off the hydrochloric acid, spin dry, add excess ethyl acetate, heat to reflux, dissolve the solid, and filter off the insoluble matter while it is hot , spin off most of the ethyl acetate, put it in ice, and a solid precipitates out. The yield of 3-(4-hydroxyphenyl)propanamide was 84%.

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Abstract

The invention discloses a synthesis method of 3-(4-hydroxyphenyl)propanamide. P-hydroxyphenylpropionic acid used as the raw material is subjected to continuous two-step reaction to prepare the 3-(4-hydroxyphenyl)propanamide. The reaction system composed of thionyl chloride and ammonia water is utilized instead of the original reaction system composed of nitrophenol, dicyclohexylcarbodiimide and ammonia methanol solution. The thionyl chloride and ammonia water are used as both reactants and solvents in the reaction, thereby greatly lowering the cost. The method avoids using dicyclohexylcarbodiimide, so that the after-treatment is more convenient; the reaction time is reduced to from 4.5 hours to 2 hours; and the yield is also enhanced from 75% to 84%.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of 3-(4-hydroxyphenyl)propionamide. Background technique [0002] 3-(4-hydroxyphenyl)propionamide (Phloretamide), a class of phenolic compounds in apples, exhibits anti-aging, prevents skin sagging, and maintains skin luster and other activities. It is also produced as an anti-aging compound or as a component of an anti-aging compound. In order to study the biological activity of 3-(4-hydroxyphenyl)propanamide, a simple and efficient chemical synthesis method is needed. [0003] There is mainly one kind of chemical synthesis method at present, which is the synthesis method reported in the US patent. This method has a total of 2 steps, and the total yield is 75% (US 2008 / 0249334 A1). Its synthetic route is as follows: [0004] [0005] The first step uses p-nitrophenol and DCC, which is not only costly, but also troublesome after DCC. [0006] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/34C07C231/02
Inventor 胡昆樊志强任杰
Owner CHANGZHOU UNIV
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