Hydrochloric Acid → 4-(5-Phenyl-pentyloxy)-butyric acid

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 228 mg, 5.7 mmol) was added to a solution of sodium 4-hydroxybutyrate (600 mg, 4.76 mmol) in N,N-dimethylformamide (5 mL). The reaction was heated at 60° C. for 1 h, then (5-bromopentyl)-benzene (1.15 g, 5.08 mmol) was added, then after 3 weeks 1 M aq. hydrochloric acid solution was added and the reaction mixture evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced 4-(5-phenyl-pentyloxy)-butyric acid (32 mg, 3%) as a colorless oil.

Provenance & Evidence