Ethylparaben → HCID 21319307, compound

Participants

Reaction Steps

To a solution of sodium (0.58 g.; 0.025 M.) in absolute ethanol (15 ml.) was added ethyl 4-hydroxybenzoate (4.15 g; 0.025 M.) in absolute ethanol (20 ml.) and the mixture was stirred at room temperature for 15 minutes. A solution of 1-bromo-14-(4-chlorophenoxy)-tetradec-9-yne (7.00 g.; 0.0175 M.) in absolute ethanol (20 ml). was added and the mixture was boiled under reflux with stirring for 6 hours. The reaction mixture was cooled to room temperature filtered and the solvent removed under reduced pressure. Dichloromethane (100 ml.) was added to the residual oil, the solution was washed with 5% sodium hydroxide solution (2×100 ml.), saturated sodium chloride solution (1×100 ml.), dried and evaporated. The oil thus produced was purified by chromatography on silica-gel (250 g.) in dichloromethane to give 1-(4-ethoxycarbonylphenoxy)-14-(4-chlorophenoxy)-tetradec-9-yne (3.76 g.; 44%) M.P. 52°-53° C.

Provenance & Evidence