Ethanol → Ethyl 8-bromooctanoate

Participants

Reaction Steps

Thionylchloride (8.15 ml, 0.112 mols) was added dropwise to an ethanol (500 ml) solution of 8-bromooctanoic acid (50.0 g, 0.224 mols) with cooling with ice, and the reaction mixture was then stirred for 12 hours at room temperature. The reaction mixture was concentrated in vacuo, and a saturated aqueous sodium bicarbonate solution was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The thus-obtained crude product was purified by alumina column chromatography (hexane) to obtain the entitled compound (51.6 g) as an oil.

Provenance & Evidence