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Preparation method of trans-4,4'-(1-bromophenyl)-cyclohexanol

A technology of cyclohexanol and bromophenyl, applied in the field of organic compound preparation, can solve problems such as unfavorable industrialized production, potential safety hazards, low product yield, etc., achieve large-scale industrialized production, overcome high cost, and high quality yield Effect

Active Publication Date: 2014-01-01
烟台海川化学制品有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Defects of this route: in the process of product synthesis, acetyl chloride is used, which is volatile at room temperature and highly toxic, and there are safety hazards in the operation of personnel. Under the condition of concentrated sulfuric acid, the nitration reaction is carried out, the selectivity of the reaction is poor, and the purity is not high. , the diazotization reaction has high requirements on the process, and a large amount of highly toxic nitrogen oxide gas will be produced during large-scale production, which has a relatively large safety hazard, and the product has poor purity, which requires multiple refining to obtain high-purity product, and the reaction route is long, each step needs to be refined and purified, the final product yield is low, and the cost is high, which is not conducive to industrial production
[0007] The raw material cost of this route is high, the selectivity of catalyst is poor, the safety of reaction process is not high, and the product yield of single step is low, and bromination reaction product yield is 40%, and the yield of final product is only 20%, is unfavorable for large-scale production. batch industrial production

Method used

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  • Preparation method of trans-4,4'-(1-bromophenyl)-cyclohexanol
  • Preparation method of trans-4,4'-(1-bromophenyl)-cyclohexanol

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Under the protection of nitrogen (30ml / min) at 20-30°C, trans-1-(4-phenyl-cyclohexyl)-ethanone (0.8mol, 161.6g), aluminum trichloride (0.8 mol, 106.8g), ferric chloride (0.24mol, 38.9g), dichloroethane (1100g). After stirring and cooling down to 2°C, bromine (1.2mol, 192g) was added dropwise, and the temperature was controlled at -5-10°C. During the dropwise addition, nitrogen gas (30ml / min) was used to discharge the hydrogen bromide produced by the reaction into the tail gas absorption system. After 1-3 hours of dripping, keep warm at -5-10°C for 2 hours. After the heat preservation is over, pour the reaction solution into ice water dissolved in NaOH (0.5mol, 20g) for hydrolysis. After liquid separation, the obtained organic phase was washed with water until pH = 7, and the solvent was removed to obtain 230.3 g of crude product, GC: 85.0%, and 175.5 g of II, GC: 99.1%. Yield 78%. mp: 58~60℃. MS (m / Z): 282 (M + ), 280 (M + ), 264, 262, 237, 235, 184, 182, 171, 169...

Embodiment 2

[0033]Under the protection of nitrogen (30ml / min) at 20-30°C, put 1-(4-phenyl-cyclohexyl)-ethanone (0.8mol, 161.6g), aluminum trichloride (0.8mol, 106.8 g), ferric chloride (0.16mol, 26g), dichloroethane (1100g). After stirring and cooling down to 2°C, bromine (1.2mol, 192g) was added dropwise, and the temperature was controlled at -5-10°C. During the dropwise addition, nitrogen gas (30ml / min) was used to discharge the hydrogen bromide produced by the reaction into the tail gas absorption system. After 1-3 hours of dripping, keep warm at -5-10°C for 2 hours, and then pour the reaction solution into ice water dissolved in NaOH (0.5mol, 20g) for hydrolysis. After liquid separation, the organic phase was washed with water until pH = 7, and the solvent was removed to obtain 231.1 g of crude product, GC: 82.5%, and 171.0 g of II, GC: 99.0%. Yield 76%. mp: 58~60℃. MS (m / Z): 282 (M + ), 280 (M + ), 264, 262, 237, 235, 184, 182, 171, 169, 154, 143, 129, 116, 103, 90, 71, 55, 51....

Embodiment 3

[0036] Under the protection of nitrogen (30ml / min) at 20-30°C, put 1-(4-phenyl-cyclohexyl)-ethanone (0.8mol, 161.6g), aluminum trichloride (0.8mol, 106.8 g), ferric chloride (0.4mol, 64.9g), dichloroethane (1100g). After stirring and cooling down to 2°C, bromine (1.2mol, 192g) was added dropwise, and the temperature was controlled at -5-10°C. During the dropwise addition, nitrogen gas (30ml / min) was used to discharge the hydrogen bromide produced by the reaction into the tail gas absorption system. After 1-3 hours of dripping, keep warm at -5-10°C for 2 hours, and then pour the reaction solution into ice water dissolved in NaOH (0.5mol, 20g) for hydrolysis. After liquid separation, the obtained organic phase was washed with water until pH = 7, and the solvent was removed to obtain 225.1 g of crude product, GC: 81.7%, and 164.2 g of II, GC: 98.9%. Yield 73%. mp: 58~60℃. MS (m / Z): 282 (M + ), 280 (M + ), 264, 262, 237, 235, 184, 182, 171, 169, 154, 143, 129, 116, 103, 90, ...

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Abstract

The invention relates to a preparation method of trans-4,4'-(1-bromophenyl)-cyclohexanol, which comprises the following steps: by using high-selectivity Lewis acid as a catalyst, a green environment-friendly strong oxidizer, and trans-1-(4-phenyl-cyclohexyl)-ethylone and bromine as initial raw materials, carrying out bromization, oxidation and hydrolysis to obtain the product trans-4,4'-(1-bromophenyl)-cyclohexanol, wherein the hydrolysis is directly carried out without purification in the intermediate oxidation reaction to synthesize the trans-4,4'-(1-bromophenyl)-cyclohexanol, the yield is 76.5%, and the GC is 99.5%. The method has the advantages of high catalyst selectivity, high product quality and yield, simple and safe operational process, short production cycle and lower raw material cost, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a preparation method of trans-4,4'-(1-bromophenyl)-cyclohexanol, belonging to the technical field of organic compound preparation. Background technique [0002] Trans-4,4′-(1-bromophenyl)-cyclohexanol is widely used in medicine, functional materials, spices, etc., and is an important intermediate in organic synthesis. Trans-4,4′-(1-bromophenyl)-cyclohexanol is an important intermediate of a new liquid crystal material developed. It introduces terminal bromine on the basis of summarizing the advantages and disadvantages of terminal cyanide and fluorine. On the one hand, it can Convert -Br to -F, -CN, etc. as required. On the other hand, the hydroxyl group is oxidized to a carbonyl group. Due to the activity of the carbonyl group, changes and reactions of various end groups are easily realized. [0003] Trans-4,4′-(1-bromophenyl)-cyclohexanol is an important intermediate for the preparation of thin and high-end liquid crystal di...

Claims

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Application Information

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IPC IPC(8): C07C35/50C07C27/02
CPCC07C29/095C07C45/63C07C67/42C07C35/50C07C69/63C07C49/567
Inventor 马振东赵青山李树国熊章宏宫振山张维维谢丽丽
Owner 烟台海川化学制品有限公司
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