Benzaldehyde, 4-(phenylmethoxy)- → HCID 12134921, compound

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diisopropylamide (LDA) (26 mL, 52 mmol, 2 M in tetrahydrofuran) was cooled to −78° C. and then added to a solution of 2-Phenoxypropionic acid ethyl ester (10 g, 51 mmol) in anhydrous tetrahydrofuran (THF) (80 mL) also cooled to −78° C. under an atmosphere of nitrogen. After 30 min, 4-benzyloxybenzaldehyde (10 g, 47 mmol) was added in one portion. After stirring over night, the reaction mixture was quenched with saturated solution of aqueous NH4Cl (10 mL) and the mixture allowed to warm to ambient temperature. The biphasic mixture was diluted with dichloromethane and partitioned, and the organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified in silica to provide colorless oil (8.9 g, 47%), Rf=0.30 in 10:1 ethyl acetate: petroleum ether.

Provenance & Evidence