Isovaleric Acid → Chloromethyl 3-methylbutanoate

Participants

Reaction Steps

1.532 g of isovaleric acid (1), 5.04 g of NaHCO3 and 0.518 g of tetrabutylammonium hydrogen sulfate were dissolved in a mixture solution of 50 ml of water and 50 ml of dichloromethane, and this mixture was ice-cooled. Then, to this mixture was added 3.025 g of chloromethyl-chlorosulfonate, and the reaction mixture was stirred for 0.5 hour at the same temperature and for 3 hours at room temperature. After the reaction, the organic layer was separated, washed with saturated saline solution and dried over magnesium sulfate. After removal of the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane: chloroform=3:1) to give 1.38 g (60%) of isovaleryloxy-methylchloride [Compound (2)].

Provenance & Evidence