Methanol → 3,3-Diphenylpentanedial

Participants

Reaction Steps

To a rapidly stirring solution of 14.24 g(0.04 mole) of diethyl 3,3-diphenylglutarate, prepared by the method of H. Ivanov and I. Anghelova, Comptes Rendus Acan. Bul. Sci., 18 (6), 529-32(1965), in 320ml of dry toluene at -78° C. under argon was added 61.12 ml (0.11 mole) of 1.86M DIBAL in toluene solution (Aldrich) over a period of 4 minutes. After 40 minutes, 40 ml of methanol was added over 4 minutes to the -78° C., stirring reaction mixture. After an additional 5 minutes of stirring, 80 ml of water was added over a 5 minute period while keeping the temperature of the reaction at -78° C. The reaction mixture was allowed to warm to room temperature and was stirred an addititional hour. The reaction mixture was filtered and the precipitated salts washed with 300 ml of warmed toluene (100° C.) and then 300 ml of boiling methylene chloride. The organic phase of the filtrate was separated, dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo giving a clear oil. The oil was used in the next step without further purification.

Provenance & Evidence