5-(Benzyloxy)-2-hydroxybenzaldehyde → 4-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenol

Participants

Reaction Steps

A solution of phenol (Kappe, T.; Witoszynskyj, T. Arch. Pharm. (1975), 308 (5), 339-346) (1.14 g, 5.00 mmol) in THF (15 mL) was cooled in a dry ice/acetone bath and treated dropwise with phenyllithium (7.5 mL, 13.5 mmol, 1.8M in cyclohexane/ethyl ether 70/30). The reaction mixture was allowed to warm gradually to ambient temperature. After 18 h, the reaction was quenched with aqueous saturated NH4Cl solution (1 mL) and partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL). The organic layer was washed with brine (75 mL), dried (Na2SO4), and concentrated to a brown oil (2.3 g). The crude product was purified by flash chromatography using hexanes:ethyl acetate (3:1 to 2:1) to give a pale yellow oil (1.42 g, 93%): 1H NMR (400 MHz, CDCl3) δ2.79 (s, 1H), 4.92 (s, 2H), 5.95, (s, 1H), 6.51 (s, 1H), 6.81 (d, 3H, J=1.5 Hz), 7.28-7.38 (s, 10H); MS (ES) m/e 305 [M−1].

Provenance & Evidence