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The synthetic method of sagrellate intermediate 2-[2-(3-methoxyphenyl) ethyl] phenol

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

Active Publication Date: 2018-04-20
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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  • The synthetic method of sagrellate 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: 300ml of triethyl phosphite was added to 100g of m-methoxychlorobenzene, and the mixture was heated to The reaction was refluxed for 1.5h. After the reaction, triethyl phosphite was recovered under reduced pressure. Then, 136g o-benzyloxybenzaldehyde and 400ml absolute ethanol were added to the residue. The reaction was refluxed for 8h. After the solvent was recovered, ice water was added and stirred. , Filter to obtain 390g 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene wet product;

[0013] (2) Synthesis of 2-[2-(3-methoxyphenyl)ethyl]phenol: add the wet product obtained in the previous step to 500ml of 80% methanol, and add 6g of 5% palladium on carbon as a catalyst, then pass Add 15 atm hydrogen gas, hydrogenate until the system does not absorb hydrogen, remove palladium carbon by filtration, recover methanol under reduced pressure, then cool and separate to obtain the lower product oil layer. Add 200ml...

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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 present invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 2-[2-(3-methoxyphenyl)ethyl]phenol, an intermediate of sargravel ester. Background technique: [0002] 2-[2-(3-Methoxyphenyl)ethyl]phenol is the key intermediate of the antithrombotic drug Sargresil Hydrochloride. Due to the low melting point of this intermediate, the current technology uses the oily substance of this intermediate The next step is to synthesize sargredate, resulting in high impurities, poor color, difficult purification, and high cost of the final product. However, the reported synthetic route has the disadvantages of numerous steps, harsh reaction conditions, large amount of three wastes and low yield, which is not conducive to industrial production. Summary of the invention: [0003] The technical problem to be solved by the present invention is to provide a method for synthesizing 2-[2-(3-methoxyphenyl)ethyl]phenol, an i...

Claims

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Application Information

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Patent Type & Authority Patents(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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