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A kind of preparation method of p-(2-methoxy)ethylphenol

A technology of ethyl phenol and chloroethyl phenol, which is applied in the field of organic synthetic medicinal chemistry, can solve problems such as difficult access to raw materials, difficulty in industrialization, and difficulty in post-processing, and achieve the effects of improved convenience, easy reaction, and low cost

Active Publication Date: 2021-09-28
ZHEJIANG YONGTAI TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] This route uses p-methoxyphenylethanol as raw material, and undergoes steps such as bromination and methoxy substitution, but the raw materials are not easy to obtain, and a large excess of hydrobromic acid is used for bromination, which makes post-processing difficult and relatively polluting, and methoxy substitution It also needs to use a large excess of sodium methoxide, and the yield is low and the cost is high
[0016] In summary, the current synthesis of p-(2-methoxy)ethylphenol generally has problems such as low yield, high cost, heavy pollution, and great difficulty in industrialization

Method used

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  • A kind of preparation method of p-(2-methoxy)ethylphenol
  • A kind of preparation method of p-(2-methoxy)ethylphenol
  • A kind of preparation method of p-(2-methoxy)ethylphenol

Examples

Experimental program
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Effect test

Embodiment 1

[0058]

[0059] Add 115g of p-chlorophenol, 260g of toluene, 3g of concentrated sulfuric acid into a 1L four-neck flask, stir evenly, and slowly introduce 120g of isobutylene at an internal temperature lower than -10°C. Quenched with % NaOH, washed again with 60 g of 30% NaOH, washed once with 60 g of water, removed toluene, and concentrated to obtain intermediate I-Cl (150 g, purity 99.2%, yield 90%).

Embodiment 2

[0061]

[0062] Add 150g of p-bromophenol, 350g of toluene, 5g of concentrated sulfuric acid into a 1L four-neck flask, stir evenly, and slowly feed 130g of isobutylene at an internal temperature lower than -10°C for 4 hours, keep at -10°C-0°C for 12h, add 120g of 30 Quenched by % NaOH, washed again with 60g of 30% NaOH, washed once with 60g of water, toluene was removed, and the product was concentrated to obtain intermediate I-Br (161g, purity 98.3%, yield 81%).

Embodiment 3

[0064]

[0065] Add 23g magnesium chips, 150g THF, N 2 Protection, heating at 65°C, dissolving 150g of intermediate I-Cl obtained in Example 1 in 150g THF and adding slowly, keeping the reaction at 72°C for 16h, cooling the reaction solution to 0-10°C, slowly adding 43g of ethylene oxide dropwise, After the addition, keep warm at 10°C for 2 to 3 hours, add 300g of 30% sulfuric acid solution dropwise, extract with 150g of toluene, wash the organic phase with 100g of water once, dry, recover toluene and THF, and obtain 150g of intermediate II crude product with a purity of 91%. 88%. The crude product can be directly subjected to the next reaction or purified by vacuum distillation to obtain 120 g of pure product with a purity of 99%.

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PUM

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Abstract

The present invention uses p-chlorophenol as a raw material, prepares p-chlorophenol protected by phenolic hydroxyl group through etherification reaction, and then generates p-(2-methoxy)ethylphenol through Grignard reaction, chlorination and methoxyl substitution reaction. The new method for preparing p-(2-methoxy)ethylphenol of the present invention has easy-to-obtain raw materials, mild reaction conditions, high safety factor, strong operability, simple process and easy industrialization, and high product purity and stable quality. It fully complies with the requirements for use as a pharmaceutical intermediate.

Description

technical field [0001] The invention relates to the field of organic synthesis medicinal chemistry, more specifically, relates to a new method for preparing a metoprolol intermediate: p-(2-methoxy)ethylphenol. Background technique [0002] p-(2-methoxy)ethylphenol is a key intermediate in the synthesis of drug metoprolol. Metoprolol (metoprolol) is an aminopropanol drug, a selective β1 receptor blocker, and is the drug of choice for the treatment of hypertension in the world in recent years. It competes with excitatory epinephrine and norepinephrine, and protects the heart at the receptor's site, inhibits cardiac contractility, prevents hyperexcitability, and blocks nerve impulses. It also ensures the contraction of the smooth muscle of the heart wall by itself. And it also has a good curative effect on angina pectoris caused by hypoxia. [0003] The synthesis of p-(2-methoxy)ethylphenol mainly includes the following: [0004] Synthetic route 1: [0005] [0006] Thi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/06C07C43/225C07C41/26C07C43/23C07C37/055C07C39/24C07C41/16C07C43/178
CPCC07C37/055C07C41/06C07C41/16C07C41/26C07C43/225C07C43/23C07C39/24C07C43/1783
Inventor 孔佳辉邵杰伟黄邦国
Owner ZHEJIANG YONGTAI TECH CO LTD
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