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Synthetic method of sarpogrelate intermediate 2-[2-(3-methoxyphenyl)ethyl]phenol

A technology of methoxyphenyl and sarcogrelate, applied in the field of synthesis of sarcogrelate intermediate 2-[2-ethyl]phenol, can solve the problems of low melting point, harsh reaction conditions, poor color, etc., and achieve simplification Effects of processing steps and loss rate reduction

Active Publication Date: 2016-08-31
安徽修一制药有限公司
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Problems solved by technology

[0002] 2-[2-(3-methoxyphenyl) ethyl] phenol is the key intermediate of the antithrombotic drug sagrelate hydrochloride, because the intermediate melting point is low, the current technology is to use the oily substance of the intermediate Synthesize sarcogrelate in the next step, resulting in high impurities, poor color, difficult purification and high cost of the final product
The reported synthetic routes have the disadvantages of many steps, harsh reaction conditions, large amount of three wastes and low yields, which are not conducive to industrial production

Method used

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  • Synthetic method of sarpogrelate intermediate 2-[2-(3-methoxyphenyl)ethyl]phenol

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Embodiment 1

[0012] (1) Synthesis of 1-benzyloxy-2-[2-(3-methoxyphenyl) vinyl] benzene: add 300ml triethyl phosphite in 100g m-methoxychlorobenzene, the mixture is warming up to Reflux reaction for 1.5h, after the reaction was completed, triethyl phosphite was recovered under reduced pressure, and then 136g of o-phenylmethoxybenzaldehyde and 400ml of absolute ethanol were added to the raffinate, and the reaction was refluxed for 8h. After the solvent was recovered, ice water was added and stirred , filtered to obtain 390g 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene wet product;

[0013] (2) Synthesis of 2-[2-(3-methoxyphenyl) ethyl] phenol: the wet product of the product obtained in the previous step is added in 500ml 80% methanol, and 6g 5% palladium carbon is added as a catalyst, and then Introduce hydrogen at 15 atm, hydrogenate until the system does not absorb hydrogen, remove palladium carbon by filtration, recover methanol under reduced pressure, then cool and separate layers to ...

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Abstract

The invention discloses a synthetic method of a sarpogrelate intermediate 2-[2-(3-methoxyphenyl)ethyl]phenol and relates to the technical field of organic synthesis. In the method, with m-methoxyl chlorobenzene, which is easy to obtain and is low in cost, as a raw material, the method includes the steps of: 1) performing condensation to the raw material with triethyl phosphite; and 2) performing condensation with o-phenylmethoxyl benzaldehyde (which is prepared from salicylic acid and chlorobenzene), performing hydrogenation to alkylate a double bond, and crystallizing a product with petroleum ether to prepare a white crystal target product. The method simplifies process steps, reduces loss ratio and is 99.5% in product purity. The 2-[2-(3-methoxyphenyl)ethyl]phenol is used for preparing sarpogrelate hydrochloride, wherein single impurity is less than 0.1% in content and the product purity reaches more than 99.8%.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 2-[2-(3-methoxyphenyl)ethyl]phenol, a sarcogrelate intermediate. Background technique: [0002] 2-[2-(3-methoxyphenyl) ethyl] phenol is the key intermediate of the antithrombotic drug sagrelate hydrochloride, because the intermediate melting point is low, the current technology is to use the oily substance of the intermediate Synthesize sarcogrelate in the next step, resulting in high impurities, poor color, difficult purification and high cost of the final product. The reported synthetic routes have the disadvantages of many steps, harsh reaction conditions, large amount of three wastes and low yields, which are not conducive to industrial production. Invention content: [0003] The technical problem to be solved by the present invention is to provide a method for synthesizing 2-[2-(3-methoxyphenyl)ethyl]phenol, a sarcogrelate intermediate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/20C07C43/23
CPCC07C41/20C07C41/30C07F9/1414C07C43/215C07C43/23
Inventor 董来山
Owner 安徽修一制药有限公司
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