Hydrochloric Acid → ethyl 4-oxodecanoate

Participants

Reaction Steps

PCC (1.2 g, 2.71 mmol) was added to a solution of 4-hydroxydecanoic acid (830 mg, 4.4 mmol) in dichloromethane (30 ml), and the mixture was stirred at room temperature for five hours. The reaction mixture was adjusted to pH 1 by adding 1 N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue was then dissolved in ethanol (15 ml). Five drops of sulfuric acid were added and the mixture was stirred at 80° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give ethyl 4-oxodecanoate (440 mg, 46% in two steps).

Provenance & Evidence