Tert-butyl 4-(1-phenylvinyl)benzoate → 1,1-Dimethylethyl 4-(1-phenylethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-(1-phenylvinyl)benzoate (0.59 g, 2.1 mmol) and palladium on carbon (10%, 100 mg) in methanol (20 mL) was stirred at 20° C. under hydrogen atmosphere (4 atm) for 24 hours. Once the start material has been consumed, the resultant mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to give tert-butyl 4-(1-phenylethyl)benzoate (500 mg, 84%). 1H NMR (300 MHz, CD3OD): δ 7.85 (d, J=4.8 Hz, 2H), 7.30-7.15 (m, 7H), 4.19-4.16 (m, 1H), 1.61 (d, J=7.2 Hz, 3H), 1.50 (s, 9H).

Provenance & Evidence