Water → alpha-[p-(1-Cycloheptenyl)-phenoxy]-undecanoic acid ethyl ester

Participants

Reaction Steps

10 g of p-(1-cycloheptenyl)-phenol in a little absolute ethanol are first added to a solution of 1.6 g of sodium in 100 ml of absolute ethanol, which is stirred at room temperature whilst excluding water; 25.2 g of α-bromo-undecanoic acid ethyl ester are then added dropwise, the mixture is left at 50°C for 24 hours, the ethanol is removed in vacuo and the residue is partitioned between ether and ice-cold 1 N sodium hydroxide solution. The organic phase is washed until neutral, dried over sodium sulphate and concentrated by evaporation in vacuo. Crude α-[p-(1-cycloheptenyl)-phenoxy]-undecanoic acid ethyl ester boiling at 160° C/0.06 mm Hg is obtained in the evaporation residue.

Provenance & Evidence