Sodium borohydride → (2-{[4-(Hydroxymethyl)phenyl]methyl}phenyl)methanol

Participants

Reaction Steps

Sodium borohydride (7.6 g) was added to 200 ml of diglyme, and with stirring at room temperature, a solution of 39.3 g of 4-(2-ethoxycarbonylbenzyl)benzaldehyde in 50 ml of diglyme was added dropwise over the course of 25 minutes. Subsequently, a solution of 9.33 g of anhydrous aluminum chloride in 50 ml of diglyme was added dropwise over the course of 15 minutes. The mixture was stirred at room temperature for 2 hours, and then at 45° to 50° C. for 1 hour. The reaction mixture was poured into about 3 liters of ice water, and stirred. The precipitated crystals were collected by filtration, washed with water, dried, and recrystallized from benzene to afford 28.2 g of 4-(2-hydroxymethylbenzyl)benzyl alcohol as colorless needle-like crystals having a melting point of 101.5° to 102° C.

Provenance & Evidence