Water → HCID 2769545, compound

Participants

Reaction Conditions

Reaction Steps

Borane-methylsulphide complex (12 ml.) was added to a stirred solution of 2-[4-(4-chlorophenyl)-phenyl]acetic acid (24.7 g.) in tetrahydrofuran (100 ml.), maintained at 4° C. and under an atmosphere of nitrogen. After 1 hour at 4° C., the reaction mixture was allowed to warm up to room temperature and was then stirred for an additional 20 hours. The excess borane was then decomposed by careful addition of water (50 ml.) to the stirred reaction mixture. Ethyl acetate (200 ml.) and a saturated aqueous solution of sodium hydrogen carbonate (200 ml.) was then added to the mixture. After separation, the organic phase was washed with water, dried (MgSO4) and evaporated. The residue was recrystallised from a mixture of hexane and toluene to give 2-[4-(4-chlorophenyl)phenyl]-ethanol (21.5 g.), m.p. 113°-115° C.

Provenance & Evidence