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Synthetic method of 3 '-methyl propiophenone

A technology of methyl propiophenone and methyl phenyl propanol, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of hydroxyl compounds, etc., can solve the problems of large consumption of oxidants, serious environmental pollution, and difficulty in recycling and reuse. , to achieve the effect of high yield, good selectivity and good stability

Pending Publication Date: 2020-07-10
惠泽化学科技(濮阳)有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In the last step of the method, the reaction from alcohol to ketone is a chemical oxidation method, and the consumption of the oxidizing agent used is large, it is difficult to recycle and reuse, the environmental pollution is serious, and it is not conducive to industrial production and application.

Method used

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  • Synthetic method of 3 '-methyl propiophenone
  • Synthetic method of 3 '-methyl propiophenone
  • Synthetic method of 3 '-methyl propiophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A 1L three-neck flask containing 1mol / L ethylmagnesium bromide tetrahydrofuran solution (700mL) was placed in an ice-water bath, and a mixture of m-tolualdehyde (0.6mol, 72.09g) and tetrahydrofuran (40mL) was added dropwise thereto. Solution, control the reaction temperature not to exceed 10°C. After the dropwise addition, the reaction was stirred at room temperature for 2 h, and then tetrahydrofuran was recovered by distillation under reduced pressure. The flask was then placed in an ice-water bath, and a 10% by mass hydrochloric acid solution was added dropwise therein, and the temperature was controlled not to exceed 10° C. until the pH of the system was neutral. Stand to separate the layers, separate the organic phase, then extract the aqueous phase with dichloromethane, combine the organic phases and concentrate to obtain a light yellow liquid, namely 3'-methylphenylpropanol. The content of 3'-methylpropanol measured by liquid chromatography is 98%.

[0038] The ...

Embodiment 2

[0040] A 1L three-neck flask equipped with 1mol / L ethylmagnesium chloride tetrahydrofuran solution (600mL) was placed in an ice-water bath, and a mixed solution composed of m-tolualdehyde (0.5mol, 60.08g) and tetrahydrofuran (20mL) was added dropwise thereto, Control the reaction temperature not to exceed 10°C. After the dropwise addition, the reaction was stirred at room temperature for 2 h, and then tetrahydrofuran was recovered by distillation under reduced pressure. The flask was then placed in an ice-water bath, and a 10% by mass hydrochloric acid solution was added dropwise therein, and the temperature was controlled not to exceed 10° C. until the pH of the system was neutral. Stand to separate the layers, separate the organic phase, then extract the aqueous phase with dichloromethane, combine the organic phases and concentrate to obtain a light yellow liquid, namely 3'-methylphenylpropanol. The content of 3'-methylpropanol measured by liquid chromatography is 98%.

[...

Embodiment 3

[0043] A 1L three-neck flask containing 1mol / L ethylmagnesium bromide tetrahydrofuran solution (700mL) was placed in an ice-water bath, and a mixture of m-tolualdehyde (0.6mol, 72.09g) and tetrahydrofuran (40mL) was added dropwise thereto. Solution, control the reaction temperature not to exceed 10°C. After the dropwise addition, the reaction was stirred at room temperature for 2 h, and then tetrahydrofuran was recovered by distillation under reduced pressure. The flask was then placed in an ice-water bath, and a 10% by mass hydrochloric acid solution was added dropwise therein, and the temperature was controlled not to exceed 10° C. until the pH of the system was neutral. Stand to separate the layers, separate the organic phase, then extract the aqueous phase with dichloromethane, combine the organic phases and concentrate to obtain a light yellow liquid, namely 3'-methylphenylpropanol. The content of 3'-methylpropanol measured by liquid chromatography is 98%.

[0044]Add t...

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Abstract

The invention belongs to the field of organic synthesis, and discloses a synthetic method of 3 '-methyl propiophenone. The method comprises the following steps: taking m-tolualdehyde as a raw material, carrying out affinity addition reaction with an ethyl Grignard reagent to obtain 3 '-methyl phenylpropanol; and then using oxygen as an oxidizing agent, using a composite catalyst composed of nitroxide free radicals, inorganic bromide and nitrite, and performing catalytic oxidation on 3 '-methyl phenylpropanol to generate 3'-methyl propiophenone. The adopted composite catalyst is good in stability and selectivity, high in yield (up to 90% or above), reusable, safe and environment-friendly in the whole process and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a synthetic method of 3'-methylpropiophenone. Background technique [0002] Bupropion analogues are representative drugs of the new generation for the treatment of depression. They have good therapeutic effect and less side effects, and have a wide demand in clinical treatment. 3'-Methylpropiophenone is a key intermediate for the preparation of bupropion analogues. [0003] WO 2010131145 discloses a method for generating 3'-methylpropiophenone by Suzuki coupling reaction with 3'-bromopropiophenone and methylboronic acid under palladium-catalyzed conditions: [0004] [0005] The cost of reaction raw materials and catalysts in this method is too high and has no industrial value. [0006] Literature (Erbing, E., Vzquez-Romero, A., Gimez, A.B., Prats, E.P, Carson, F., Zou, X., Tolstoy, P., Mart, B., Matute, M. General, simple, and chemoselective catalysts for the isomerization o...

Claims

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Application Information

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IPC IPC(8): C07C45/39C07C49/76C07C29/40C07C33/20
CPCC07C45/39C07C29/40C07C33/20C07C49/76
Inventor 马青松刘睿苏健刘娇朱华志王晓莺赖彭莹马心旺田维波郑玉奇
Owner 惠泽化学科技(濮阳)有限公司
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