Manufacturing method of bicyclohexyl derivative
A technology of bicyclohexane and a manufacturing method is applied in the field of manufacture of bicyclohexane derivatives, can solve the problems of difficult isomerization trans isomer, difficult isomerization into trans isomer and the like, and achieves high selectivity and yield effect
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Embodiment 1
[0049] [Preparation of 4'-ethyl-bicyclohexyl-4-carboxylic acid]
[0050] 0.50 g (2.2 mmol) of 4'-ethyl-biphenyl-4-carboxylic acid and 2 ml of acetic acid were put into an autoclave with a capacity of 50 ml, and 10% palladium / carbon (50% wet product manufactured by Kawaken Fine Chemical Co., Ltd.) was added. ) 100mg as palladium catalyst.
[0051] After the above feeding was completed, the pressure in the autoclave was raised to 0.5 MPa with nitrogen, and then the depressurization operation was repeated three times to replace nitrogen in the system. Next, use hydrogen to replace the system with hydrogen according to the same operation as the above-mentioned nitrogen replacement, then raise the temperature in the system, and adjust it so that the hydrogen pressure in the system is 0.4 MPa when it reaches 125°C, so as to provide the hydrogenation required. The theoretical hydrogen amount of hydrogen.
[0052] After the hydrogenation reaction was carried out at 125° C. for 16 ho...
Embodiment 2
[0055] [Preparation of 4'-propyl-bicyclohexyl-4-carboxylic acid]
[0056] 0.50 g (2.1 mmol) of 4'-propyl-biphenyl-4-carboxylic acid and 2 ml of distilled water were put into an autoclave with a capacity of 50 ml, and 10% palladium / carbon (50% wet product manufactured by Kawaken Fine Chemical Co., Ltd.) was added. ) 100mg as palladium catalyst.
[0057] After the above feeding was completed, the pressure in the autoclave was raised to 0.5 MPa with nitrogen, and then the depressurization operation was repeated three times to replace nitrogen in the system. Next, use hydrogen to replace the system with hydrogen according to the same operation as the above-mentioned nitrogen replacement, then raise the temperature in the system, and adjust it so that the hydrogen pressure in the system is 0.4 MPa when it reaches 125°C, so as to provide the hydrogenation required. The theoretical hydrogen amount of hydrogen.
[0058] After the hydrogenation reaction was carried out at 125° C. for...
Embodiment 3-1
[0061] [Preparation of 4'-acetyl-biphenyl-4-carboxylic acid]
[0062]
[0063] 2 g of biphenyl was dissolved in 10 ml of o-dichlorobenzene, 4.5 g of aluminum chloride and 2.14 ml of diethylcarbamoyl chloride were added, and stirred at 100° C. for 4 hours. The reaction liquid was cooled to 30°C, and 1.01 ml of acetyl chloride was added dropwise (internal temperature was below 40°C). After stirring at 40° C. for 1 hour, the reaction solution was cooled to room temperature, and added dropwise to 20 ml of ice water. After extraction with ethyl acetate and washing with saturated brine, the organic layer was concentrated under reduced pressure and purified by column chromatography to obtain 3.5 g of 2.
[0064] 3.5 g of 2 was dissolved in 32 ml of 12N hydrochloric acid water, and stirred at 130° C. for 24 hours. The reaction solution was cooled to room temperature, and the crystals were filtered and washed with water. Add 1 L of methanol to the obtained crystals, boil and wash...
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