4-Methylbenzaldehyde → HCID 13316494, compound

Participants

Reaction Steps

A solution of L-phenylalaninol (6.0 g) and 4-methylbenzaldehyde (5.3 g) in ethanol (40 ml) was stirred for 30 minutes at room temperature. Sodium borohydride (2.0 g) was added in small portions with stirring and ice-cooling, and then the mixture was stirred for 1.5 hours at room temperature. After removal of the ethanol by evaporation, the residue was acidified with dilute hydrochloric acid and then made alkaline with aqueous sodium hydroxide. The resulting mixture was extracted with chloroform. The extract was dried over sodium sulfate and the solvent was evaporated. The residue was recrystallized from ethanol to give N-(4-methylbenzyl)-L-phenylalaninol (8.9 g), mp 125°-127° C., [α]D -6.7°.

Provenance & Evidence