Diethyl Malonate → diethyl 2-(2-methylallyl)malonate

Participants

Reaction Steps

Sodium (5.08 g.) was dissolved in dry ethanol (300 ml.). Diethyl malonate (35 g.) was added and the mixture was stirred for 2 hours. Methallyl chloride (20 g.) was added and the mixture was refluxed with stirring for 4 hours. The mixture was cooled, the solid filtered off and the solvent was removed in vacuo. 2N Hydrochloric acid solution was added and the mixture was extracted with diethyl ether. The ethereal extracts were washed with sodium hydrogen carbonate solution, water and then dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. Distillation gave diethyl 2-methyl-prop-2-enylmalonate as a colourless liquid (28.2 g. b.p. 120°-126° 20 mm.).

Provenance & Evidence