Phenyl-3-pyridinylmethanone → Phenyl(pyridin-3-yl)methanol

Participants

Reaction Steps

50.0 gms of phenyl-3-pyridyl ketone was added to 650 ml of methanol and the system was then cooled to 0° to 5° C. After cooling, 15.5 gms of sodium borohydride was added in 3 parts. After addition, the system was allowed to come to room temperature. The system was then refluxed for 1 hour and stirred for an additional 72 hours at room temperature. The methanol was removed by stripping. Afterwards, 575 ml of 5% HCl solution was added to the residue and the system refluxed for 15 minutes. The acid was neutralized with 50% NaOH solution and the product extracted with methylene chloride to give the 3-pyridylphenylcarbinol as a white solid, m.p. 53° to 60° C.

Provenance & Evidence