Ethyl 5-bromovalerate → 5-[p-(1-Cyclooctenyl)-phenoxy]-pentanoic acid ethyl ester

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Reaction Steps

12 g of p-(1-cyclooctenyl)-phenol are first added to a solution of 1.7 g of sodium in 60 ml of absolute ethanol whilst stirring in an anhydrous atmosphere, and after 30 minutes 18.8 g of 5-bromopentanoic acid ethyl ester are added dropwise. After completion of the addition, the mixture is stirred for 15 hours at 70° C and is evaporated to dryness in vacuo. The evaporation residue is distributed between 3 times 150 ml of ether and twice 100 ml of water. The organic phases are combined, dried over sodium sulphate and evaporated in vacuo. Chromatography of the evaporation residue on silica gel with chloroform as the eluant gives 5-[p-(1-cyclooctenyl)-phenoxy]-pentanoic acid ethyl ester of boiling point 165° -170° C at 0.03 mm Hg.

Provenance & Evidence