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A kind of preparation method of 4-trans-(4'-bromo-biphenyl-4-yl)-cyclohexanol

A technology of biphenyl and cyclohexanol, applied in the field of organic compound preparation, to achieve the effects of easy operation of synthesis process conditions, low energy consumption and low cost

Active Publication Date: 2014-10-29
烟台海川化学制品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no relevant literature report on the synthesis of this compound at present, so it is of great significance to find a method for synthesizing 4-trans-(4'-bromo-biphenyl-4-yl)-cyclohexanol

Method used

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  • A kind of preparation method of 4-trans-(4'-bromo-biphenyl-4-yl)-cyclohexanol
  • A kind of preparation method of 4-trans-(4'-bromo-biphenyl-4-yl)-cyclohexanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Pass nitrogen gas (20-30ml / min) to protect the system, put 34.3g of 4,4'-dibromobiphenyl and 500g of THF into a 1L three-necked bottle successively, stir and dissolve completely, cool down to -70-80℃, add 55ml dropwise n-BuLi (2mol / l), exothermic violently, temperature control -70~-80℃, keep warm for 1h. After the heat preservation is completed, add dropwise a solution of 15.6g 1,4-cyclohexanone monoethylene glycol ketal and 60g THF, control the reaction system to -70~-80°C and add dropwise, and keep warm for 2h. After the heat preservation is completed, pour 500ml of ice water into it for hydrolysis, and extract the water phase with 600g of toluene to obtain the toluene solution of III.

[0025] The toluene solution in the above step Ⅲ is used as raw material, and 1.9g TsOH·H 2 O, nitrogen (20-30ml / min) protection, stirring to raise the temperature, reflux to separate water, the temperature is 105-110°C, and the reaction is kept for 3-5h. After the heat preservation ...

Embodiment 2

[0030] Pass nitrogen gas (20-30ml / min) to protect the system, put 34.3g of 4,4'-dibromobiphenyl and 500g of THF into a 1L three-necked bottle successively, stir and dissolve completely, cool down to -70-80℃, add 60.5 ml n-BuLi (2mol / l), exothermic violently, control the temperature to -70~-80°C, keep warm for 1h. After the heat preservation is completed, add dropwise a solution of 15.6g 1,4-cyclohexanone monoethylene glycol ketal and 60g THF, control the reaction system to -70~-80°C and add dropwise, and keep warm for 2h. After the heat preservation is completed, pour 500ml of ice water into it for hydrolysis, and extract the water phase with 600g of toluene to obtain the toluene solution of III.

[0031] The toluene solution in the above step Ⅲ is used as raw material, and 1.9g TsOH·H 2 O, nitrogen (20-30ml / min) protection, stirring to raise the temperature, reflux to separate water, the temperature is 108-110°C, keep the reaction for 3-5h. After the heat preservation is co...

Embodiment 3

[0036] Pass nitrogen gas (20-30ml / min) to protect the system, put 34.3g of 4,4'-dibromobiphenyl and 500g of THF into a 1L three-necked bottle successively, stir and dissolve completely, cool down to -70--80℃, add 66ml dropwise n-BuLi (2mol / l), exothermic violently, temperature control -70~-80℃, keep warm for 1h. After the heat preservation is completed, add dropwise a solution of 15.6g 1,4-cyclohexanone monoethylene glycol ketal and 60g THF, control the reaction system to -70~-80°C and add dropwise, and keep warm for 2h. After the heat preservation is completed, pour into 500ml of ice water for hydrolysis, and extract the water phase with 600g of toluene to obtain the toluene solution of III.

[0037] The toluene solution in the above step Ⅲ is used as raw material, and 1.9g TsOH·H 2 O, nitrogen (20-30ml / min) protection, stirring to raise the temperature, reflux to separate water, the temperature is 108-110°C, and the reaction is kept for 3-5 hours. After the heat preservati...

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Abstract

The invention relates to a preparation method of 4-trans-(4'-bromine-biphenylyl-4-yl)-cyclohexanol. By adopting the method, a high-selectivity FeBr3 and Pd / C composite catalyst is adopted to carry out brominated double-bond hydrogenation, so that bromide-removed by-products which are difficulty purified are avoided; 4,4'-dibromobiphenyl is taken as a raw material to prepare the compound 4-trans-(4'-bromine-biphenylyl-4-yl)-cyclohexanol by a butyl lithium reaction, an addition reaction, a dehydration reaction, a hydrogenation reaction, a decondensation reaction and a reduction reaction. According to the 4-trans-(4'-bromine-biphenylyl-4-yl)-cyclohexanol, the total yield is 80%, the purity is 99.8% and the melting point is 210.0-210.5 DEG C. The catalyst selected by the method disclosed by the invention is high in selectivity, product quality and yield, simple and safe in operation processes, and low in raw material cost; industrial production is facilitated.

Description

technical field [0001] The invention relates to a preparation method of 4-trans-(4'-bromo-biphenyl-4-yl)-cyclohexanol, belonging to the technical field of organic compound preparation. Background technique [0002] 4-trans-(4'-bromo-biphenyl-4-yl)-cyclohexanol is widely used in medicine, functional materials, spices, etc., and is an important intermediate in organic synthesis. [0003] 4-trans-(4'-bromo-biphenyl-4-yl)-cyclohexanol has the stability of biphenyl-based liquid crystals and the low viscosity of cyclohexane-based liquid crystals. It is a very effective additive, and the research on this type of compound has been highly valued by people. This type of liquid crystal also has unique photoelectric properties and excellent mechanical properties, so it is used in nonlinear optics, full-color imaging display, fast optical switch, microelectronics, and as a high-strength, high-modulus polymer material in military, aerospace and other fields. It has broad application pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C35/50C07C29/143
Inventor 赵青山李树国冯绍全杨德飞赵峰李纪松龙亚周
Owner 烟台海川化学制品有限公司
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