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A kind of preparation method of pharmaceutical intermediate p-methoxypropiophenone

A technology of p-methoxybenzene and methoxybenzoic acid, which is applied in the field of preparation of pharmaceutical intermediate p-methoxypropiophenone, can solve problems such as high product cost, difficult separation and purification, and unsatisfactory results, and achieve Low cost, simple separation and purification process, and short reaction time

Inactive Publication Date: 2011-11-30
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because it is easy to generate a mixture of m-methoxypropiophenone and o-methoxypropiophenone with a relatively close boiling point in the process of acid chloride reaction, it is difficult to separate and purify, and the separation requires a solvent method, the operation process is complicated, and the product yield is low
The synthetic method of other relevant p-methoxypropiophenone, its result is all not ideal enough
Also because of the specificity of the product in the synthesis method and some difficulties in the process, the product yield is extremely low, resulting in high product costs

Method used

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  • A kind of preparation method of pharmaceutical intermediate p-methoxypropiophenone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a four-necked reaction flask equipped with an electric stirrer, a reflux condenser and a thermometer, add 15.2 g of p-methoxybenzoic acid, 44.4 g of propionic acid, and 7.5 g of a composite catalyst in sequence. After the addition, start stirring to control the condensation reaction temperature The temperature is about 135-145°C, and the condensation reaction is carried out by stirring for 7-13h, and the excess propionic acid is distilled off, and the temperature continues to rise until the gas begins to escape at 275°C, and the decarboxylation reaction is carried out at the temperature of 275-285°C. Use 95% ethanol solution to absorb the escaped gas and the distilled liquid. After 1-2h, there is no liquid distilled out in the four-necked reaction bottle, then stop the reaction, then cool and crystallize to obtain the p-methoxypropiophenone product. The yield of methoxypropiophenone reaches 71.25%, and the melting point is 27-28°C.

Embodiment 2

[0021] In a four-necked reaction flask equipped with an electric stirrer, a reflux condenser and a thermometer, add 15.2 g of p-methoxybenzoic acid, 51.8 g of propionic acid, and 7.5 g of a composite catalyst in sequence. After the addition, start stirring to control the condensation reaction temperature The temperature is about 135-145°C, and the condensation reaction is carried out by stirring for 7-13h, and the excess propionic acid is distilled off, and the temperature continues to rise until the gas begins to escape at 275°C, and the decarboxylation reaction is carried out at the temperature of 275-285°C. Use 95% ethanol solution to absorb the escaped gas and the distilled liquid. After 1-2h, there is no liquid distilled out in the four-necked reaction bottle, then stop the reaction, then cool and crystallize to obtain the p-methoxypropiophenone product. The yield of methoxypropiophenone reaches 71.05%, and the melting point is 27-28°C.

Embodiment 3

[0023] In a four-necked reaction flask equipped with an electric stirrer, a reflux condenser, and a thermometer, add 15.2 g of p-methoxybenzoic acid, 59.2 g of propionic acid, and 7.5 g of a composite catalyst in sequence. After the addition, start stirring to control the condensation reaction temperature The temperature is about 135-145°C, and the condensation reaction is carried out by stirring for 7-13h, and the excess propionic acid is distilled off, and the temperature continues to rise until the gas begins to escape at 275°C, and the decarboxylation reaction is carried out at the temperature of 275-285°C. Use 95% ethanol solution to absorb the escaped gas and the distilled liquid. After 1-2h, there is no liquid distilled out in the four-necked reaction bottle, then stop the reaction, then cool and crystallize to obtain the p-methoxypropiophenone product. The yield of methoxypropiophenone reaches 71.68%, and the melting point is 27-28°C.

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Abstract

The invention discloses a preparation method of a medical intermediate p-methoxypropiophenone, which uses p-methoxybenzoic acid and propionic acid as raw materials to prepare p-methoxypropiophenone by reacting in the presence of a composite catalyst; The composite catalyst is composed of iron powder, manganese oxide and thorium oxide. The present invention uses p-methoxybenzoic acid and propionic acid as raw materials to synthesize p-methoxypropiophenone under the action of the composite catalyst. The separation and purification process is simple and the reaction time is short. Short, high product yield, so that the product yield reaches more than 71%, high product purity, low energy consumption, small environmental pollution, low cost, is an ideal process for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate p-methoxypropiophenone. Background technique [0002] p-methoxypropiophenone is an aromatic asymmetric ketone compound, a white crystalline solid, with a melting point of 27-28°C and a boiling point of 273-275°C. p-methoxypropiophenone is an important structural compound intermediate. Mainly used as pharmaceutical intermediates, key intermediates for the synthesis of anti-premature drug ritodrine (1-(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethylamino]propanol) 2-Bromo-4-methoxypropiophenone. [0003] Its chemical name is: p-methoxypropiophenone [0004] Molecular formula: C 10 h 12 o 2 ;Molecular weight: 164.2 [0005] Molecular formula: [0006] [0007] Physical and chemical properties: Appearance is white crystal, melting point mp: 27-28℃, boiling point bp: 273-275℃. [0008] At present, the existing synthetic method of p-methoxypropiophenone is the acyl chlori...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/48
Inventor 王树清高崇汤艳峰石玉军苏广均
Owner NANTONG UNIVERSITY
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