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Preparation of phenol 2-[2-(3-methoxyphenyl) ethyl]

A technology of methoxyphenyl and m-methoxybenzaldehyde is applied in the field of preparation of 2-[2-(3-methoxyphenyl)ethyl]phenol, which can solve the problems of long reaction steps, complicated operation, Water-free requirements are high, and the effect of mild reaction conditions and simple post-processing can be achieved.

Inactive Publication Date: 2008-10-08
CHINA PHARM UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] (1) Raw materials are not easy to obtain;
[0012] (2) Due to the existence of the salicylaldehyde phenolic hydroxyl group, its reaction yield with the Grignard reagent is low;
[0013] (3) Grignard reaction requires high anhydrous, and anhydrous ether is used as a solvent, which is flammable and explosive, and is not suitable for industrial production;
[0014] (4) The reaction steps are long and the total yield is low
[0019] (1) Raw materials are not easy to obtain;
[0020] (2) Use expensive triphenylphosphine to prepare Wittig reagent. Wittig reaction requires high anhydrous, and post-reaction treatment requires column chromatography separation, which is cumbersome to operate and is not suitable for industrial production;
[0021] (3) Low yield

Method used

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  • Preparation of phenol 2-[2-(3-methoxyphenyl) ethyl]
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  • Preparation of phenol 2-[2-(3-methoxyphenyl) ethyl]

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Experimental program
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Effect test

Embodiment 1

[0040] The preparation of embodiment 1,2-benzyloxybenzaldehyde (III):

[0041] Add 100ml of anhydrous acetone, 12.2g of salicylaldehyde (II), 13.2g of benzyl chloride, and 15.3g of potassium carbonate into the reaction flask, stir, heat to reflux for 2h, filter, concentrate the filtrate under reduced pressure, add 50ml of ethyl acetate and 30ml of water , the organic layer was dried with anhydrous sodium sulfate, filtered, concentrated and solidified, and recrystallized from ethanol to obtain 19.4 g of white needle-like crystals, yield 91.5%, mp 45-46°C.

[0042] 1 HNMR (CDCl 3 )δ: 10.56 (1H, s, -C H O) 7.01~7.78 (9H, m, Ar-H), 5.19 (2H, s, PhC H 2 O-).

Embodiment 2

[0043] The preparation of embodiment 2,2-benzyloxybenzyl alcohol (IV):

[0044] Add 10.5 g of 2-benzyloxybenzaldehyde (III) and 60 ml of anhydrous methanol into the reaction flask, slowly add 1.7 g of sodium borohydride in an ice bath, raise to room temperature, stir for 3 h, adjust the pH to 7 with dilute hydrochloric acid, and concentrate the reaction solution Afterwards, it was dissolved in 30 ml of ethyl acetate, washed with water, the organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain 10.1 g of a colorless oil, with a yield of 95.3%.

[0045] 1 HNMR (CDCl 3 )δ: 7.03~7.51 (9H, m, Ar-H), 5.21 (2H, s, PhC H 2 O-), 4.83 (2H, s, -C H 2 OH)2.34(1H,s,-CH 2 o H ).

Embodiment 3

[0046] Embodiment 3, the preparation of 2-benzyloxybenzyl chloride (V):

[0047] Add 9.5g of 2-benzyloxybenzyl alcohol (IV) and 40ml of toluene into the reaction bottle, slowly add 2.4g of phosphorus trichloride dropwise, after the dropwise addition, stir at room temperature for 4h, and then add 1N sodium hydroxide solution, saturated sodium bicarbonate The solution and 20ml of water were washed successively, the organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain 9.8g of light yellow oil.

[0048] 1 HNMR (CDCl 3 )δ: 6.98~7.55 (9H, m, Ar-H), 5.17 (2H, s, PhC H 2 O-), 4.57 (2H, s, -C H 2 Cl).

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Abstract

The invention discloses a new method to synthesize 2-[2-(3-methoxyphenyl)-ethyl] phenol(I). The new method is characterized in that the method takes salicylaldehyde as material to prepare 2-benzyloxy-benzyl chloride through benzyl protection, deoxidization and cl-substitution; 2- benzyloxy-benzyl chloride is turned to [[2-(benzyloxy) phenyl] methyl] diethyl phosphonate through Arbuzov reaction and then 1-benzyloxy-2-[2-(3-methoxyphenyl) ethylene] benzene is obtained through Witting-Hommer reaction; finally, 2-[2-(3-methoxyphenyl)-ethyl] phenol(I) is obtained through catalytic hydrogenation. The invention also discloses new intermediate compounds in the syntheticroute of synthesize 2-[2-(3- methoxyphenyl)-ethyl] phenol(I).

Description

technical field [0001] Process for the preparation of 2-[2-(3-methoxyphenyl)ethyl]phenol. Background technique [0002] Sarpogrelate hydrochloride (Sarpogrelate hydrochloride, Anbu Leke, SARP), the following structural formula is 5-hydroxytryptamine (5-HT) listed by Mitsubishi Pharmaceutical Co., Ltd. 2 ) receptor blocker, Anbu Leke tablet was launched in China in 2001; this product can specifically interact with 5-HT 2 Receptor binding, suitable for the improvement of ischemic symptoms such as chronic thromboangiitis obliterans accompanied by ulcers, pain and cold sensation. [0003] [0004] 2-[2-(3-methoxyphenyl) ethyl] phenol (I) is the important intermediate of synthetic sarcogrelate hydrochloride, structural formula is as follows: [0005] [0006] According to literature reports, there are mainly two synthetic routes: [0007] 1° Journal of Medicinal Chemistry 27(2), 645-649; 1984 reported route: [0008] Using 3-methoxybenzyl chloride as raw material, make ...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/30
Inventor 陈国华王生张海军
Owner CHINA PHARM UNIV
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