Benzyl Alcohol → (3'-Benzyloxybiphenyl-2-yl)methanol

Participants

Reaction Steps

A solution of benzyl 2-(3′-benzyloxyphenyl)benzoate from Step D (1.35 g, 3.42 mmol) in dry THF (20+10 mL) was added dropwise to a stirred suspension of LiAlH4 (0.26 g, 6.84 mmol) in THF (30 mL) at 0° C., under argon. Stirring was continued for 1 hour at 0° C., then the reaction was quenched with wet ether, followed by water, then aq. NH4Cl. The resulting mixture was extracted with EtOAc (2×100 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a crude product which contained benzyl alcohol. Vacuum distillation (1 mm Hg, 80° C.) allowed removal of most of the benzyl alcohol to give the titled product as a pale solid.

Provenance & Evidence