2-(Benzyloxy)-3-(tert-butyl)benzaldehyde → (2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)methanol

Participants

Reaction Steps

A solution of 2-(benzyloxy)-3-tert-butylbenzaldehyde (5.4 g, 20 mmol) was stirred under nitrogen on an ice bath and 1M phenyl magnesium bromide (30 mL, 1.5 equiv) was added at such a rate that temperature did not exceed 7° C. Stirring was continued at room temperature for 2 hr. The reaction mixture was cooled on an ice bath and quenched with saturated ammonium chloride (50 mL). The resulting mixture was partitioned between water (25 mL) and 1:1 ethyl acetate/heptane (150 mL). The organic layer was washed with brine (100 mL), dried over sodium sulfate and the solvent was removed in a rotary evaporator. The crude product (7.3 g) was purified by chromatography on silica (75 g) with heptane (0.5 L) and 2.5% ethyl acetate in heptane (2 L) to produce 13 (5.4 g, 78%) as a pale yellow oil.

Provenance & Evidence