Hydrochloric Acid → HCID 178516057, compound

Participants

Reaction Conditions

Reaction Steps

0.76 g (20 mmols) NaBH4 was suspended in 30 ml THF under nitrogen and cooled to 0° C. A solution of 4.16 g 4-(3-fluoro-4-hydroxyphenyl)cyclohexanone in 50 ml THF was added dropwise at the same temperature over a period of 15 minutes, and the resulting mixture was stirred at 0° C. until no more of the starting material was present. 10 ml 25% HCl was then added dropwise at a temperature of between 0-10° C., and stirred for a further 30 minutes. The reaction mixture was then poured into 100 ml of water and extracted three times with 50 ml of diethyl ether. The combined organic phases were washed twice with 50 ml of water, dried over magnesium sulphate and filtered. Removal of the solvent and recrystallisation of the residue from isopropanol gave 2-fluoro-4-(trans-4-hydroxycyclohexyl)phenol.

Provenance & Evidence