Benzyl Alcohol → Benzyl 4-bromobutanoate

Participants

Reaction Conditions

Reaction Steps

80% Sodium hydride dispersion in oil (0.18 g, 5.9 mmol) was added portionwise to a stirred solution of benzyl alcohol (0.64 g, 5.9 mmol) in anhydrous tetrahydrofuran (10 ml) under nitrogen. After a further 1 hour at room temperature, the reaction mixture was cooled to -70° C. and a solution of 4-bromobutanoyl chloride (1.0 g, 5.4 mmol) in anhydrous tetrahydrofuran (3 ml) added dropwise. After 0.5 hour, the cooling bath was removed and the reaction mixture quenched at room temperature with 5% aqueous ammonium chloride solution (20 ml) and then extracted with dichloromethane (3×20 ml). The combined extracts were washed with saturated brine, dried (Na2SO4) and evaporated under reduced pressure, then the residue was purified by column chromatography on silica gel, eluting with dichloromethane, to give the required ester as a gum. Rf 0.60 (SS 16).

Provenance & Evidence