反应详情

温度

0 °C

The 1-(4-propylphenyl)-4-(4-oxocyclohexyl)-1-cyclohexene described above in an amount of 9.5 g (32 mmol) was dissolved in mixed solvent of 200 ml of THF and 50 ml of ethanol, and cooled down to 0° C. Sodium borohydride in an amount of 1.2 g (32 mmol) was gradually added thereto and the mixture was stirred at the same temperature for 1 hour. The reaction solution was added in 150 ml of 1N hydrochloric acid and extracted with diethyl ether. After the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn, the solvent was distilled off under a reduced pressure. The residue was dissolved in 80 ml of mixed solvent of ethanol/ethyl acetate (1/1), the solution was subjected to a hydrogenation by using Raney Nickel catalyst, and then the catalyst was filtered off. The solvent was distilled off and then the residue was recrystallized by using toluene to give 2.5 g (8.3 mmol) of 4-(4-(4-hydroxycyclohexyl)cyclohexyl)-1-propylbenzene. Yield of this compound was 26%.

1. extractionextracted with diethyl ether
2. washAfter the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn
3. distillationthe solvent was distilled off under a reduced pressure
4. dissolutionThe residue was dissolved in 80 ml of mixed solvent of ethanol/ethyl acetate (1/1)
5. filtrationthe catalyst was filtered off
6. distillationThe solvent was distilled off
7. customthe residue was recrystallized