Process for preparing 6-[3-(1-adamantyl)-4-methoxy phenyl]-2-methyl naphthoate

A technology of methyl naphthoate and methoxyphenyl, which is applied in the field of preparation of methyl 6-[3--4-methoxyphenyl]-2-naphthoate, can solve the three wastes, high cost and industrialization Production difficulties and other problems, to achieve the effect of reducing three wastes, easy operation, and increased yield

Inactive Publication Date: 2006-09-06
JIANGSU ZHONGDAN GROUP +2
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Problems solved by technology

Document US4717720 has reported the laboratory synthesis of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid methyl ester, using p-bro...

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  • Process for preparing 6-[3-(1-adamantyl)-4-methoxy phenyl]-2-methyl naphthoate
  • Process for preparing 6-[3-(1-adamantyl)-4-methoxy phenyl]-2-methyl naphthoate
  • Process for preparing 6-[3-(1-adamantyl)-4-methoxy phenyl]-2-methyl naphthoate

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Embodiment Construction

[0011] Preparation of 2-(1-adamantyl)-4-bromophenol

[0012] Add 13g of p-bromophenol, 11.4g of 1-adamantol and 250ml of dichloromethane into a 500ml reactor, stir and dissolve, add 3.75ml of concentrated sulfuric acid dropwise at room temperature, and continue the reaction for 8 hours. The reaction mixture was poured into 250ml of water, the layers were separated, and the dichloromethane layer was washed with saturated NaHCO 3 The solution was washed until nearly neutral, and the lower organic phase was separated and concentrated to obtain a crude product. The crude product was dissolved with 600ml of mixed solvent petroleum ether / ethyl acetate (5:1), separated by simple chromatography on a silica gel column, and eluted with petroleum ether / ethyl acetate (5:1) (TLC tracking, developing solvent was petroleum Ether / ethyl acetate=5 / 1, Rf value=0.4), the eluent was vacuum precipitated to obtain 18.8g white solid, yield 81.5%, melting point: 138-140°C.

[0013] Preparation of 2-...

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Abstract

The invention relates to a method for preparation of methyl 6-[3-(1-adamantyl)-4-methoxylphenyl]-2- naphthoate. It consisits of synthesizing 2-(1-adamantyl)-4-bromophenol by coupling reaction between bromophenol and adamantine alcohol, synthesizing 2-(1-adamantyl)-4-bromoanisole by methylating reaction between the obtained 2-(1-adamantyl)-4-bromophenol and the methyliodide, then gaining the Grignard reagent by 2-(1-adamantyl)-4-bromoanisole and magnesium initiated by one or more than one of iodine, iodide and bromide in the solvent of ethers or non-polar solvent, and finally synthesizing the said methyl 6-[3-(1-adamantyl)-4-methoxylphenyl]-2-naphthoate by reaction between methyl 6- bromine-2-naphthoate and the said Grignard reagent. The invention is characterized in that its side reaction is decreased, its product quality is improved, its stocks are all normal chemical products of localization of manufactures, its operation is simple, and the three wastes are reduced, the cost is reduced, so it is suitable for industrial production of large scale.

Description

technical field [0001] The invention relates to a preparation method of methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoate. Background technique [0002] Methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoate as the main intermediate and starting point for the synthesis of the third-generation retinoid drug adapalene raw material. Document US4717720 has reported the laboratory synthesis of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid methyl ester, using p-bromophenol as raw material, the yield is 36.95%, industrialization The production is difficult, and the cost is high, and the three wastes are serious. [0003] Contents of the invention [0004] In order to solve the above problems, the present invention provides a method for preparing methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoate. [0005] Preparation method of the present invention can be represented by following reaction formula: [0006] [0007] [0008] Using the method of the ...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/76
Inventor 张家庆陈捷周春红翟富荣周玉琢龚熙见
Owner JIANGSU ZHONGDAN GROUP
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