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Para-(2-methoxyl) ethylphenol synthesis method

A technology of ethyl phenol and synthesis method, which is applied in the directions of alkylene oxide preparation of ether, ether preparation, organic chemistry, etc., can solve the problems of poor synthesis selectivity and large production pollution, and achieves less three wastes, high product yield and high purity. Effect

Active Publication Date: 2009-04-29
SHANDONG HANXING PHARM TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are also people who use p-nitrotoluene as starting material to synthesize p-(2-methoxy)ethylphenol, but this reaction route also has the problems of poor synthesis selectivity and large production pollution. The synthesis process can use the following chemical reaction The equation says:

Method used

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  • Para-(2-methoxyl) ethylphenol synthesis method
  • Para-(2-methoxyl) ethylphenol synthesis method
  • Para-(2-methoxyl) ethylphenol synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Add 128 grams (1.0mol) of p-chlorophenol, 500ml of toluene, and 2 grams of concentrated sulfuric acid in a 1000ml three-necked flask, and pass through isobutylene under water bath cooling conditions to react until more than 90% of p-chlorophenol is converted into p-chlorophenyl tert-butyl After ether, the isobutene was stopped. Cool to a lower temperature and terminate the reaction with 30% aqueous sodium hydroxide solution and wash to remove unreacted p-chlorophenol, and then wash with water until nearly neutral. The obtained p-chlorophenyl tert-butyl ether toluene solution was concentrated to obtain about 420 grams of toluene solution containing about 40% p-chlorophenyl tert-butyl ether for the next reaction.

Embodiment 2

[0021] Add 172 grams (1.0mol) of p-bromophenol, 500ml of toluene, and 2 grams of concentrated sulfuric acid in a 1000ml three-necked flask, and pass through isobutylene under water bath cooling conditions to react until more than 90% of p-bromophenol is converted into p-bromophenyl tert-butyl After ether, the isobutene was stopped. Cool to a lower temperature and terminate the reaction with 30% sodium hydroxide aqueous solution and wash to remove unreacted p-bromophenol, and then wash with water until nearly neutral. The obtained toluene solution of p-bromophenyl tert-butyl ether was concentrated to obtain about 420 grams of toluene solution containing about 40% of p-bromophenyl tert-butyl ether for the next reaction.

Embodiment 3

[0023] Add 500ml tetrahydrofuran, 24 grams (1.0mol) magnesium in 2000ml there-necked flask, add about 5-10% of the reaction solution of the previous step under reflux conditions to initiate the reaction, and then control the dropwise addition of the parachlorine obtained in the step reaction under reflux conditions. After the dropwise addition of the phenyl tert-butyl ether toluene solution is completed, it is refluxed until the p-chlorophenyl tert-butyl ether reacts substantially completely to obtain a Grignard reaction solution. Then, under cooling conditions, 48.4 grams (1.1 mol) of ethylene oxide was slowly added to react to obtain p-tert-butoxyphenethyl alcohol. The reaction solution was washed with water, separated into layers to obtain an organic phase, and the organic phase was concentrated and rectified to obtain about 125 grams of p-tert-butoxyphenethyl alcohol (purity>95%).

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Abstract

The invention discloses a method for synthesizing phenetyl, which uses p-chlorophehol or p-bromophenol as starting reaction raw material. It first uses methyl, benzyl or tert-butyl to protect the phenolic hydroxyl, the parivis which is protected by the phenolic hydroxyl reacts with the magnesium in the ether, tetrahydrofuran, tert-butyl methyl ether, isopropyl ether and its mixing solution to obtain the Grignard reagent, the Grignard reagent directly reacted with the etox to obtain the tyrosol which is protected by the phenolic hydroxyl, the tyrosol reacts with the dimethyl sulfate, dimethyl carbonate, trimethyl orthoformate to obtain the tyrosol ether which is protected by phenolic hydroxyl, which obtains the product in acid or hydrogenation protection.

Description

technical field [0001] The present invention relates to a kind of synthetic method that has at least one hydroxyl group or oxygen-metal base to be connected on the compound of six-membered aromatic ring carbon atom, relate to a kind of p-(2-methoxyl group) ethylphenol more specifically resolve resolution. Background technique [0002] P-(2-methoxy)ethylphenol (4-(2-methoxyethyl)phenol) is the key intermediate of the synthetic drug metoprolol, and its structural formula is as follows: [0003] P-(2-methoxy)ethylphenol is generally obtained by using phenylethyl alcohol as a starting material, and is obtained through multi-step reactions and purifications such as methyl etherification, nitration, reduction, diazotization and hydrolysis. The yield of synthesizing p-(2-methoxyl) ethylphenol by this method is relatively low, and the quantity of three wastes is large, and the cost of producing p-(2-methoxyl)ethylphenol is higher, and its synthetic process can be used as follows ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/02C07C43/178
Inventor 毛海舫
Owner SHANDONG HANXING PHARM TECH CO LTD
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