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Synthetic method for methyl synephrine

A technology of methyl synephrine and synthetic method, applied in the field of synthesis of methyl synephrine

Inactive Publication Date: 2015-09-02
李玉山
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] At present, there is no report about methyl synphene and synthesis process. The present invention uses simple and easy-to-obtain phenol as raw material to obtain phenol propionate through esterification, and phenol propionate undergoes Friedel-Crafts rearrangement reaction under the catalyst Obtain p-hydroxypropiophenone, which can be obtained by bromination of p-hydroxypropiophenone to produce 2-bromo-1-(4-hydroxyphenyl)acetone, which can be obtained by reacting 2-bromo-1-(4-hydroxyphenyl)acetone with methylamine 2-methylamino-1-(4-hydroxyphenyl) acetone, 2-methylamino-1-(4-hydroxyphenyl) acetone is reduced to obtain 1-(4-hydroxyphenyl)-2-( methylamino)

Method used

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  • Synthetic method for methyl synephrine
  • Synthetic method for methyl synephrine
  • Synthetic method for methyl synephrine

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Embodiment Construction

[0014] The synthetic route of the present invention is as follows:

[0015]

[0016]

[0017] 1. Preparation of phenol propionate Add 100g of phenol, 240mL of morpholine, and 130mL of benzene into a 1000mL four-necked round-bottomed flask equipped with a mechanical stirrer, a thermometer, a drying tube and a reflux condenser, and slowly add in an ice-salt bath Add 230g of propionyl chloride within 30min, raise to room temperature, continue to react to form white floc, continue to react for 1-3h, detect with thin-layer chromatography, concentrate the reaction solution, add water at 5-10℃ and stir well, static Set the layers, collect the organic phase, the water layer contains propionic acid, morpholine salt and propionyl chloride produced by the reaction, extract 2-4 times with an equal volume of benzene, combine the benzene liquid, and recover the benzene solvent under reduced pressure to obtain a colorless and transparent Phenol propionate.

[0018] 2. Preparation of p...

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Abstract

The invention provides a synthetic method for methyl synephrine, wherein easily available phenol, adopted as the raw material, is esterified to obtain phenol propionate. Through the friedel-crafts rearrangement reaction of the phenol propionate under the effect of a catalyst, para-hydroxypropiophenone is prepared. The para-hydroxypropiophenone is bromized to prepare 2-bromo-1-(4-hydroxyphenyl) acetone. The 2-bromo-1-(4-hydroxyphenyl) acetone reacts with methylamine to prepare 2-methyl amino-1-(4-hydroxyphenyl) acetone. The 2-methyl amino-1-(4-hydroxyphenyl) acetone is reduced to prepare 1-(4-hydroxyphenyl)-2-(methylamino). The synthetic method is simple to operate, mild in reaction condition, convenient in post-treatment, and high in yield. Therefore, the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing methyl synephrine. Background technique [0002] Methylsynephrine (Methylsynephrine) is also known as: methylsynephrine, 4-hydroxyephedrine, Oluofulin, Oluofulin. Molecular weight: 181.23, CAS No.365-26-42, English name: Oxilofrine, Oxyephedrini Hydrochloridum, P-Hydroxyephedrine, SuprifenHydroxy ephedrine, Oxyephrine, (R*, S*)-4-hydroxy-alpha-[1-(methylamino) ethyl]benzyl alcohol(R*,S*)-4-hydroxy-alpha-[1-(methylamino)ethyl]benzyl alcohol;Oxyephedrine;rac-4-[(1R*,2S*)-1-Hydroxy-2- (methylamino)propyl]phenol; l-(p-Hydroxyphenyl)-2-(methylami no)-1-propanol; 1-Hydroxypholedrine; 4-(1-Hydroxy-2-methylaminopropyl)phenol; 1-(methylamino)ethyl]benzenemethanol, EINECS No.206-672-3, white or off-white crystalline powder, soluble in water, insoluble in petroleum ether, chloroform and other organic solvents. m.p.209-210℃, the structural formula is as follows: [0003] [0004] Foreign studies have found ...

Claims

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Application Information

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IPC IPC(8): C07C215/60C07C213/00
CPCY02P20/584
Inventor 李玉山
Owner 李玉山
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