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

Temperature

-69 °C

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.

1. stirringfurther stirred at −70° C. for 1 hour
2. additionwas slowly added dropwise to the reaction solution at a temperature range of from −70 to −60° C
3. temperatureAfter gradually warming the reaction solution to 0° C.
4. extractionextracted with 500 mL of toluene
5. washThe resulting organic layer was washed with 1N hydrochloric acid
6. dry with materialby drying over anhydrous magnesium sulfate
7. customThereafter, the solvent was removed by distillation under reduced pressure

ORD record

ord-ba7cb27983624e488bcc74110fc11450

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07695777B2