Method for synthesizing 4-hydroxymethyl-biphenyl

A technology for hydroxymethyl biphenyl and biphenyl, which is applied in the field of synthesizing 4-hydroxymethyl biphenyl, can solve problems such as low cost, and achieve the effects of strong price advantage, cheap and easily available raw materials, and easy control of conditions.

Active Publication Date: 2018-01-19
浦拉司科技(上海)有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, also lack a kind of preparation technology simple at present, cost is low, is suitable for the 4-hydroxymethyl biphenyl synthetic method of industrial scale-up

Method used

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  • Method for synthesizing 4-hydroxymethyl-biphenyl
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  • Method for synthesizing 4-hydroxymethyl-biphenyl

Examples

Experimental program
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Effect test

Embodiment 1

[0021]

[0022] Preparation of 4-chlorobiphenyl

[0023] In a 500 mL round bottom flask, 30.8 g of biphenyl was dissolved in 250 mL of tetrahydrofuran, and 28.1 g of chlorosuccinimide was added at room temperature, and then reacted at room temperature for 36 hours. After the reaction was completed, the solvent was concentrated under reduced pressure (recovered for the next reaction), the residue was poured into water, extracted with dichloromethane, washed with water, evaporated to remove the solvent, and then recrystallized with 95% ethanol to obtain a white solid 28.3 g, yield 75%.

[0024] Preparation of 4-hydroxymethylbiphenyl

[0025] Add 4.0g metal magnesium chips, a small amount of iodine and 40mL tetrahydrofuran (recovered in the previous step) into a 500mL three-necked flask, heat to 60°C, and add dropwise 28.3g of 4-chlorobiphenyl dissolved in 130mL tetrahydrofuran (recovered in the previous step) and 13.9g of n-butyl chloride solution, dropwise, reflux reaction...

Embodiment 2

[0027]

[0028] Preparation of 4-bromobiphenyl

[0029] In a 500 mL round bottom flask, 30.8 g of biphenyl was dissolved in 250 mL of 2-methyltetrahydrofuran, 35.6 g of bromosuccinimide was added at room temperature, and then reacted at room temperature for 36 hours. After the reaction was completed, the solvent was concentrated under reduced pressure (recovered for the next reaction), the residue was poured into water, extracted with dichloromethane, then washed with water, the solvent was evaporated, and then recrystallized with 95% ethanol to obtain a white solid 35.4 g, yield 76%.

[0030] Preparation of 4-hydroxymethylbiphenyl

[0031] Add 4.0g metal magnesium chips, a small amount of iodine and 40mL 2-methyltetrahydrofuran (recovered in the previous step) into a 500mL three-necked flask, heat to 60°C, and add dropwise the solution dissolved in 180mL 2-methyltetrahydrofuran (recovered in the previous step) under nitrogen protection. 35.4g of 4-bromobiphenyl and 1.4g ...

Embodiment 3

[0033]

[0034] Preparation of 4-chlorobiphenyl

[0035] In a 250 mL round bottom flask, 15.4 g of biphenyl was dissolved in 125 mL of 2-methyltetrahydrofuran, 13.4 g of chlorosuccinimide was added at room temperature, and then reacted at room temperature for 36 hours. After the reaction was completed, the solvent was concentrated under reduced pressure (recovered for the next reaction), the residue was poured into water, extracted with dichloromethane, washed with water, evaporated to remove the solvent, and then recrystallized with 95% ethanol to obtain a white solid 13.8 g, yield 73%.

[0036] Preparation of 4-hydroxymethylbiphenyl

[0037] Add 1.9g metal magnesium chips, a small amount of iodine and 20mL 2-methyltetrahydrofuran (recovered in the previous step) into a 250mL three-necked flask, heat to 60°C, and dropwise add 2-methyltetrahydrofuran dissolved in 60mL (recovered in the previous step) under nitrogen protection 13.8g of 4-chlorobiphenyl and 6.8g of n-butyl ...

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Abstract

The invention discloses a method for synthesizing 4-hydroxymethyl-biphenyl, belonging to the field of organic synthesis. The method comprises the steps of enabling biphenyl, which is taken as a raw material, to react with NXS to generate 4-halogenated biphenyl; then, enabling the generated 4-halogenated biphenyl to react with magnesium metal in presence of chlorinated n-butane so as to generate aGrignard reagent; then, enabling the generated Grignard reagent to react with XCH2OR, and carrying out acidic hydrolysis to obtain the 4-hydroxymethyl-biphenyl. The method has the advantages of beingeasy in obtaining of raw material, low in cost and mild in conditions, thus having a process amplification prospect.

Description

Technical field: [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for synthesizing 4-hydroxymethyl biphenyl. Background technique: [0002] 4-Hydroxymethylbiphenyl is an important biphenyl derivative, which is widely used in medicine, polymer liquid crystal, dyes and so on. For example, it can be used to synthesize non-simplified anti-inflammatory drugs such as felbinac and fenbufen, anti-inflammatory and analgesic drugs such as ethyl felbinac. [0003] At present, there are mainly three kinds of synthetic methods about 4-hydroxymethyl biphenyl reported in the literature: 1) in the presence of aluminum trichloride and cuprous chloride, biphenyl reacts with carbon monoxide and hydrogen chloride mixed gas, and obtains 4- Formyl biphenyl (CN101434527 A), then 4-formyl biphenyl is reduced by sodium borohydride to obtain 4-hydroxymethyl biphenyl (TetrahedronLetters 2006,47,5261), and the cost of sodium borohydride is higher, q...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/12C07C25/18C07C29/10C07C33/24C07C41/30C07C43/164
Inventor 漆伟君肖海旺蔡伟兵
Owner 浦拉司科技(上海)有限责任公司
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