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Synthesis method of trans-4-alkyl cyclohexyl benzoic acid

A technology of cyclohexyl benzoic acid and cyclohexyl benzoate, which is applied in the field of organic chemical synthesis, can solve the problems of cyclohexyl benzene being difficult to obtain, large environmental pollution, etc., and achieves easy industrial production, little environmental pollution, and high yield. Effect

Pending Publication Date: 2020-07-03
惠泽化学科技(濮阳)有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This method has two major disadvantages, one is that the raw material containing cyclohexylbenzene with alkyl substituents is not easy to get, and the other is that there are relatively large environmental pollution problems in the two steps of the reaction process

Method used

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  • Synthesis method of trans-4-alkyl cyclohexyl benzoic acid
  • Synthesis method of trans-4-alkyl cyclohexyl benzoic acid
  • Synthesis method of trans-4-alkyl cyclohexyl benzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add trans-4-methylcyclohexylphenol (0.8mol, 153.23g), sodium carbonate (0.8mol, 84.79g), toluene (500mL) into a 2000mL three-necked flask, stir for 15min, reflux for 2 hours to remove the water in the system , The temperature was lowered to 80° C., p-toluenesulfonyl chloride (1.0 mol, 190.65 g) dissolved in anhydrous toluene was slowly added dropwise, and after the dropwise addition, the temperature was raised and refluxed for 10 hours. After the reaction, it was cooled, washed with water until the organic phase was neutral, the water phase was separated, the organic phase was distilled under reduced pressure to recover the solvent, and the remaining was cooled and dried to obtain trans-4-methylcyclohexylbenzene p-toluenesulfonate (268.71g) ), the content is 91% detected by liquid chromatography;

[0033] The prepared trans-4-methylcyclohexylbenzene p-toluenesulfonate (0.1mol, 37.86g), isopropanol (0.3mol, 18.02g), palladium dichloride (0.001mol, 0.18g), Tripheny...

Embodiment 2

[0036]

[0037] Add trans-4-ethylcyclohexylphenol (0.8mol, 163.45g), potassium carbonate (0.8mol, 110.57g), toluene (500mL) into a 2000mL three-necked flask, stir for 15min, reflux for 2 hours to remove the water in the system After the temperature was lowered to 80°C, methylsulfonyl chloride (1.0 mol, 114.56 g) was slowly added dropwise, and after the dropwise addition, the temperature was raised and refluxed for 10 hours. After the reaction, cool and wash with water until the organic phase is neutral. Separate the water phase and distill the organic phase under reduced pressure to recover the solvent. After cooling and drying, the remaining white substance is trans-4-ethylcyclohexylbenzyl sulfonic acid. Ester (233.05g), the content is 92% detected by liquid chromatography;

[0038] The prepared trans-4-ethylcyclohexylbenzenesulfonate (0.1mol, 30.67g), n-butanol (0.3mol, 22.24g), palladium acetate (0.002mol, 0.45g), bis(diphenyl) Phosphine) methane (0.002mol, 0.77g), potassium ...

Embodiment 3

[0041]

[0042] Add trans-4-propylcyclohexylphenol (0.8mol, 174.67g), triethylamine (0.8mol, 81.0g), toluene (500mL) into a 2000mL three-necked flask, stir for 15min, reflux for 2 hours to remove the With water, the temperature was lowered to 80°C and trifluoromethanesulfonyl chloride (1.0 mol, 168.52g) was slowly added dropwise. After the dropwise addition, the temperature was raised and refluxed for 10 hours. After the reaction, cool, wash with water until the organic phase is neutral, separate the water phase, and distill the organic phase under reduced pressure to recover the solvent. After cooling and drying, the remaining white substance is trans-4-propylcyclohexyltrifluoromethanesulfonic acid Ester (276.53g), the content is 93% detected by liquid chromatography;

[0043] The prepared trans-4-propylcyclohexyl trifluoromethanesulfonate (0.1mol, 36.36g), ethanol (200mL), bisacetonitrile palladium dichloride (0.001mol, 0.26g), two (diphenyl) Phosphine) ethane (0.001mol, 0.4g)...

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Abstract

The invention belongs to the field of organic chemical synthesis, and discloses a synthetic method of trans-4-alkyl cyclohexyl benzoic acid. According to the method, trans-4-alkyl cyclohexyl phenol isused as a raw material and reacts with sulfonyl chloride to generate aromatic sulfonate, a carbonyl insertion reaction of aromatic sulfonate is catalyzed by palladium to generate a trans-4-alkyl cyclohexyl benzoate compound with alkyl alcohol, and finally ester hydrolysis is performed to obtain the target product trans-4-alkyl cyclohexyl benzoic acid. The method has the advantages of mild reaction conditions, simple synthesis process, and high yield (up to 90% or above), the catalyst is safe and nontoxic and can be repeatedly used, and the synthesis method is environmentally friendly and canbe easily applied to industrial production.

Description

Technical field [0001] The invention belongs to the field of organic chemistry synthesis and relates to a method for synthesizing trans-4-alkylcyclohexyl benzoic acid. Background technique [0002] Trans-4-alkylcyclohexyl benzoic acid is an important intermediate for the synthesis of liquid crystal materials. It is also often used in the synthesis of fine chemicals such as medicines and pesticides. It is a class of compounds with very wide application value. [0003] The traditional method for synthesizing trans-4-alkylcyclohexyl benzoic acid is to produce trans-4-alkylcyclohexyl-4′-acetylbenzene by acylation reaction of alkylcyclohexylbenzene beforehand. The hypohalite is oxidized and then acidified to obtain the final product. [0004] [0005] This method has two major shortcomings. One is that it is not easy to obtain cyclohexylbenzene whose raw material contains alkyl substituents, and the other is that both steps of the reaction process have large environmental pollution probl...

Claims

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Application Information

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IPC IPC(8): C07C51/09C07C63/49
CPCC07C51/09C07C67/36C07C303/28C07B2200/09C07C2601/14C07C63/49C07C69/76C07C309/73
Inventor 马青松刘睿王晓莺刘娇苏健马心旺赖彭莹朱华志张彩霞高东峰
Owner 惠泽化学科技(濮阳)有限公司
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