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Method for synthesizing 4-[2-(trans-4-alkyl cyclohexyl )ethyl]cyclohexanone

A synthesis method and alkyl ring technology are applied in the synthesis of liquid crystal materials, in the field of synthesis of 4-[2-(trans-4-alkylcyclohexyl)ethyl]cyclohexanone, which can solve the problem of lithium aluminum hydride reagents. High price, environmental pollution and other problems, to achieve the effect of reducing raw material consumption, avoiding serious environmental pollution, and high total yield

Active Publication Date: 2013-08-28
XIAN CAIJING OPTO ELECTRICAL SCI & TECH
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  • Claims
  • Application Information

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Problems solved by technology

[0022] 4-trans-cyclohexylmethyl chloride is obtained by two-step reaction of trans-4-alkylcyclohexyl formic acid through lithium aluminum hydride reduction and chlorination. The lithium aluminum hydride reagent used in the reaction is expensive, and the chlorination reaction requires Sulfoxide, causing serious environmental pollution

Method used

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  • Method for synthesizing 4-[2-(trans-4-alkyl cyclohexyl )ethyl]cyclohexanone
  • Method for synthesizing 4-[2-(trans-4-alkyl cyclohexyl )ethyl]cyclohexanone
  • Method for synthesizing 4-[2-(trans-4-alkyl cyclohexyl )ethyl]cyclohexanone

Examples

Experimental program
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Embodiment 1

[0062] Example 1: Preparation of 4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexanone

[0063] The specific preparation steps of this embodiment are as follows:

[0064] Step 1: Synthesis of trans-4-pentylcyclohexylcarbaldehyde (B)

[0065] Under the protection of nitrogen, add 52.2g (0.6mol) morpholine and 300mL toluene into a 1000mL three-necked flask, cool down to -5°C with ice brine under stirring, and add 150g (0.52mol) red aluminum toluene solution dropwise, where the mass fraction of red aluminum 70%). After the addition, keep it warm at -5-0°C for 2 hours to prepare the reducing reagent.

[0066] Under the protection of nitrogen, add 42.5g (0.2mol) trans-4-pentylcyclohexylmethyl carboxylate and 50mL toluene into a 1000mL three-necked flask, cool down to -5°C with an ice-salt bath while stirring, and dropwise add the above-prepared Reducing reagent, after the dropwise addition, incubate at -5°C to 0°C for 2 hours. After the reaction is complete, add 120mL of concentrat...

Embodiment 2

[0076] Example 2: Preparation of 4-[2-(trans-4-ethylcyclohexyl)ethyl]cyclohexanone

[0077] The preparation method is the same as in Example 1, except that the trans-4-ethylcyclohexylmethyl carboxylate is used to replace the trans-4-pentylcyclohexylmethyl carboxylate to prepare the target product 4-[2-(trans- 4-Ethylcyclohexyl)ethyl]cyclohexanone. The melting point is 40.2°C.

Embodiment 3

[0078] Example 3: Preparation of 4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexanone

[0079] The preparation method is the same as in Example 1, except that the trans-4-propylcyclohexylmethyl carboxylate is used to replace the trans-4-pentylcyclohexylmethyl carboxylate to prepare the target product 4-[2-(trans- 4-Propylcyclohexyl)ethyl]cyclohexanone. The melting point is 45.5°C.

[0080] Other Examples: Preparation of 4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexanone

[0081] The preparation method is the same as in Example 1, except that the organic solvent N,N-dimethylformamide described in step (4) is replaced by dichloromethane, dichloroethane, toluene, acetone, and ethanol. The target product 4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexanone can be prepared.

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Abstract

The invention discloses a method for synthesizing 4-[2-(trans-4-alkyl cyclohexyl )ethyl]cyclohexanone, comprising: reducting trans-4-alkyl cyclohexyl methyl formate which is used as a raw material under action of an aluminum / morpholine reducing agent, to obtain trans-4-alkyl cyclohexyl formaldehyde; carrying out witting reaction of trans-4-alkyl cyclohexyl formaldehyde with a 4-benzyloxy triphenyl benzylidene bromide phosphine salt under action of potassium tert-butoxide, to obtain 1-benzyloxy-4-[2-(trans-4-alkyl cyclohexyl )vinyl]benzene; under catalysis of palladium on activated carbon, hydrogenating 1-benzyloxy-4-[2-(trans-4-alkyl cyclohexyl )vinyl]benzene, to obtain 4-[2-(trans-4-pentyl cyclohexyl )ethyl]cyclohexyl alcohol; and oxidizing 4-[2-(trans-4-pentyl cyclohexyl )ethyl]cyclohexyl alcohol with hydrogen peroxide, to prepare 4-[2-(trans-4-alkyl cyclohexyl )ethyl]cyclohexanone compounds. The method has advantages of few steps, low cost and high overall yield, and oxidation reaction is carried out under green hydrogen peroxide, thereby avoiding serious environment pollution caused by a metal oxidation reagent.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals and relates to the synthesis of a liquid crystal material, in particular to a synthesis method of 4-[2-(trans-4-alkylcyclohexyl)ethyl]cyclohexanone. Background technique [0002] In recent years, with the rapid development of liquid crystal display technology, higher requirements have been put forward for liquid crystal materials. Ethane-bridged liquid crystals have low viscosity, high stability, large dielectric anisotropy, and good compatibility with other liquid crystals, especially high chemical stability and good anti-ultraviolet radiation performance. It is widely used to reduce the viscosity of mixed liquid crystals, expand the range of liquid crystal phases, adjust the birefringence, etc., and can be widely used as an excellent component in the preparation of wide temperature liquid crystals. [0003] 4-[2-(trans-4-alkylcyclohexyl)ethyl]cyclohexanone is an important class of liquid...

Claims

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Application Information

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IPC IPC(8): C07C49/403C07C45/29
Inventor 高嫒嫒胡明刚杜渭松赵群星刘建韬陈龙闫晓亮李涛刘庆薛力徐磊
Owner XIAN CAIJING OPTO ELECTRICAL SCI & TECH
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