1,5-Diiodopentane → [1-(4-Chloro-benzoyl)-cyclohexyl]-acetic acid

Participants

Reaction Steps

8.4 g (0.04 mol) of 4-(4-chlorophenyl)-4-oxo-butyric acid are dissolved in 300 ml tetrahydrofuran, combined batchwise with 5.8 g (0.12 mol) of sodium hydride (50% in oil) and refluxed for 90 minutes. After the addition of 8.9 ml (0.06 mol) of 1,5-diiodopentane the reaction mixture is refluxed for a further 3 hours. After cooling the reaction mixture is stirred into ice water, the tetrahydrofuran is distilled off and the residue is extracted with methylene chloride. The aqueous phase is acidified with hydrochloric acid and extracted with methylene chloride. The combined organic extracts are dried and evaporated down. The residue is chromatographed on silica gel and eluted with methylene chloride+ethanol (1 to 2%).

Provenance & Evidence