Hydrochloric Acid → 3,3'-Difluoro-4'-(1-hydroxy-4-propylcyclohexyl)-4-propoxybiphenyl

Participants

Reaction Conditions

Reaction Steps

To a solution of 15.0 g (60.4 mmol) of the 3,3′-difluoro-4-propoxybiphenyl obtained in the first step of Example 1 in 85 ml of THF was added by drops 70 ml (1.04M, cyclohexane solution, corresponding to 72.5 mmol) of sec-butyllithium while being maintained at a temperature lower than −60° C. After finishing of the dropping, it was stirred at the same temperature for 1 hour. Subsequently, a solution of 11.0 g (78.5 mmol) of 4-propylcyclohexanone in 55 ml of THF was added by drops thereto while being maintained at a temperature of −60° C., stirred at the same temperature for 3 hours, and then further stirred at room temperature for 2 hours. After 200 ml of a diluted hydrochloric acid was added by drops to the reaction liquid, it was extracted with 200 ml of toluene. The organic layer thus obtained was washed with a diluted aqueous sodium bicarbonate solution twice and with water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography (eluent: heptane/ethyl acetate=8/2) to obtain 21.2 g of a crude 3,3′-difluoro-4′-(1-hydroxy-4-propylcyclohexyl)-4-propoxybiphenyl. (Yield: 90.6%)

Provenance & Evidence