Aluminium lithium hydride → 4-Methyl-3-phenyl-4-penten-1-ol

Participants

Reaction Conditions

Reaction Steps

The methyl 4-methyl-3-phenyl-4-pentenoate (258.3 g, 1.251 mol) was added, at 0° C. under nitrogen, to lithium aluminum hydride (25 g, 0.625 mol) in dry THF (1 liter), drop-wise. After 30 minutes, the cooling bath was removed and the reaction allowed reaching room temperature. After 24 h, more THF (1 liter) was added and the reaction was cooled to 0° C. and treated successively with water (25 ml), 5% aqueous sodium hydroxide (75 ml) and water (25 ml). The reaction was stirred at room temperature for 30 minutes. Anhydrous solid sodium sulfate was added (100 g) and stirring continued for 5 minutes The solid was filtered off, rinsed with diethyl ether and the filtrate was evaporated under vacuum. The product was purified distillation through a 20-cm Widmer column. 214 g of the desired product were obtained (yield=97%).

Provenance & Evidence