(E)-3-(4-benzyloxy-2-methyl-phenyl)-acrylic acid ethyl ester → Ethyl 3-(4-hydroxy-2-methylphenyl)propanoate

Participants

Reaction Steps

To a flask containing 10% Pd/C catalyst under nitrogen was added ethyl (2E)-3-{2-methyl-4-[(phenylmethyl)oxy]phenyl}-2-propenoate (1.22 g, 4.12 mmol) in EtOH (15 mL) washing in with more EtOH (2×4 mL). The reaction vessel was placed under an atmosphere of hydrogen and stirred rapidly at ambient temperature for 19 h. The mixture was then filtered through a pad of celite washing with EtOH and the filtrate reduced under vacuum. The residue was the purified by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 10:1 to 2:1) to afford the title compound (548 mg).

Provenance & Evidence