Diethyl Ether → 4-Methyl-3-phenyl-4-pentenal

Participants

Reaction Steps

Solid pyridinium chlorochromate (110.24 g, 0.5 mol) was added portion-wise to a pre-cooled (−10° C.) mixture of 4-methyl-3-phenyl-4-penten-1-ol (70 g, 0.418 mol) and anhydrous sodium acetate (41.5 g, 0.5 mol) in dry dichloromethane (400 ml) under nitrogen. After 30 minutes, the reaction was warmed up to room temperature. After 4 hours, diethyl ether (1 liter) was added to the reaction. After stirring for 30 minutes, the reaction was filtered through silica gel, rinsing with diethyl ether. The solvent was removed under vacuum and the residue was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 5:1) followed by distillation through a 20-cm Widmer column. 24 g (yield=33%) of the desired product were obtained. B.P.=50° C./0.001 mbar.

Provenance & Evidence