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Synthesis method for 3-methoxypropiophenone

A technology of methoxybenzene and synthesis method, which is applied in the field of synthesis of pharmaceutical intermediate compounds, can solve the problems of low yield and high cost, and achieve the effects of simple operation, low cost and advanced technology

Inactive Publication Date: 2017-03-22
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the shortcomings of high cost and low yield in the current industrial synthesis of 3-methoxypropiophenone, and provide a green synthesis method for 3-methoxypropiophenone

Method used

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  • Synthesis method for 3-methoxypropiophenone
  • Synthesis method for 3-methoxypropiophenone
  • Synthesis method for 3-methoxypropiophenone

Examples

Experimental program
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Embodiment 1

[0020] Add 24.0 g (1.0 mol) of magnesium powder, 3.0 g of anhydrous aluminum trichloride, and 300 mL of tetrahydrofuran (THF) solution into a reaction flask equipped with a reflux condenser and a dropping funnel, and heat. Slowly add a mixed solution of 187.1 g (1.0 mol) of m-methoxy bromobenzene and 300 mL of tetrahydrofuran (THF) into the dropping funnel, and control the temperature of the reaction solution to 50-55°C to keep the solution in a slightly boiling state. After the addition, heat Reflux for 0.5-1.0h to ensure complete magnesium reaction and obtain Grignard reagent. Under stirring, 55.1 g (1.0 mol) of propionitrile was slowly added to the Grignard reagent, and after the addition was completed, the reaction was carried out for another 1.0-2.0 h. After the reaction is completed, add 3.0 mol / L hydrochloric acid dropwise slowly under a cold water bath to decompose the addition product and separate the inorganic phase. The organic phase is distilled off under normal pre...

Embodiment 2

[0026] The amount of m-methoxy bromobenzene was increased to 205.7 g (1.1 mol), propionitrile was 60.5 g (1.1 mol), and others were the same as in Example 1, and the yield of 3-methoxypropiophenone was 82.5%.

Embodiment 3

[0028] The amount of m-methoxy bromobenzene was increased to 224.5 g (1.2 mol), propionitrile was 66.1 g (1.2 mol), and the other same as in Example 1, the yield of 3-methoxypropiophenone was 85.8%.

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Abstract

The invention discloses a synthesis method for 3-methoxypropiophenone. The synthesis method comprises the steps of enabling magnesium and m-bromoanisole to produce a Grignard reagent in a tetrahydrofuran (THF) solution under the catalytic action of aluminum chloride, and then, subjecting the Grignard reagent to a reaction with propionitrile, thereby producing the 3-methoxypropiophenone. According to the synthesis method, the operation is simple, the process is advanced, the solvent can be recycled, and thus, the industrial production is facilitated. According to the 3-methoxypropiophenone prepared by the synthesis method, the yield reaches 88.6%, and the liquid-phase purity reaches up to 99.44% or more.

Description

Technical field [0001] The invention belongs to the field of synthesis of pharmaceutical intermediate compounds, and specifically relates to a synthesis method of 3-methoxypropiophenone. [0002] technical background [0003] Tapentadol hydrochloride, chemical name 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol hydrochloride, is used It relieves moderate to severe acute pain in the central nervous system of adults and has good clinical efficacy. 3-Methoxypropiophenone is a key intermediate for the synthesis of tapentadol hydrochloride. At present, the traditional process for industrial production of 3-methoxypropiophenone at home and abroad uses 3-hydroxypropiophenone and dimethyl sulfate to react to obtain 3-methoxypropiophenone. -Methoxypropiophenone has high cost, many by-products, and low yield. Dimethyl sulfate is highly toxic and difficult to industrialize. Therefore, it is imperative to seek advanced technology and low production costs, and develop a gree...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/45C07C49/84
CPCC07C45/455C07F3/02C07C49/84
Inventor 李德江周洋王龙张诺诺郑开波李秀荣
Owner CHINA THREE GORGES UNIV
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