Water → 1-(4-Bromophenyl)-4-propylcyclohexanol

Participants

Reaction Conditions

Reaction Steps

37.7 g of 1,4-dibromobenzene (13) and 300 mL of THF were placed in a reactor under nitrogen atmosphere and stirred at −69° C. 100 mL of a 1.6M n-BuLi hexane solution was added dropwise thereto at a temperature range of from −69 to −62° C. over 1 hour, and then further stirred at −70° C. for 1 hour. 22.4 g of 4-propylcyclohexanone (14) dissolved in 20 mL of THF was slowly added dropwise to the reaction solution at a temperature range of from −70 to −60° C. After gradually warming the reaction solution to 0° C., the reaction solution was slowly poured into 1,000 mL of water and extracted with 500 mL of toluene. The resulting organic layer was washed with 1N hydrochloric acid, a saturated sodium bicarbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain 50.1 g of 1-(4-bromophenyl)-4-propylcyclohexanol (15). The resulting compound (15) was a yellow oily matter.

Provenance & Evidence