Ethanol → HCID 21319305, compound

Participants

Reaction Steps

Sodium (0.69 g; 0.03 M.) was dissolved in absolute ethanol (30 ml.) with protection from atmospheric moisture. Ethyl 4-hydroxybenzoate (4.98 g; 0.03 M.) in absolute ethanol (20 ml.) was added and the mixture was stirred at room temperature for 30 minutes. A solution of 1-bromo-15-(4-chlorophenoxy)-pentadecan-11-one (8.62 g. 0.02 M.) in absolute ethanol (30 ml.) was added and the mixture was boiled under reflux with stirring for 8 hours. After cooling to room temperature dichloromethane (200 ml.) was added, the mixture was extracted with 5% sodium hydroxide solution (2×100 ml.) and water (1×100 ml.). The solution was dried (MgSO4), the solvent evaporated under reduced pressure and the crude product (8.75 g.) was purified by chromatography on silica-gel (300 g.) in dichloromethane to give 1-(ethoxycarbonylphenoxy)-15-(4-chlorophenoxy)-pentadecan-11-one (5.07 g.; 33%), M.P. 95°-96° C.

Provenance & Evidence