Sulfuric Acid → Diethyl dimethylmalonate

Participants

Reaction Steps

0.023 ml of concentrated sulfuric acid are cautiously added to a solution of 4 g of 2,2-dimethylmalonic acid in 30 ml of a 1:2 absolute ethanol/toluene mixture. The reaction mixture is refluxed, distilling the azeotropic water/toluene mixture and adding every few an ethanol/toluene mixture. After 3 hours, the reaction mixture is added with 50 ml of water and extracted with ethyl acetate (3×15 ml). The combined organic extracts are dried over sodium sulfate and solvent is evaporated off under reduced pressure. The residue is purified by silica gel chromatography (eluent 2:1 hexane/AcOEt). 3.3 g of 2,2-dimethylmalonic acid diethyl ester are obtained.

Provenance & Evidence