Potassium Hydroxide → Ethyl hydrogen diethylmalonate

Participants

Reaction Steps

A solution of diethyl-malonic acid diethyl ester (3.0 g, 13.89 mmol) and potassium hydroxide (0.778 g, 13.89 mmol) in ethanol (50 ml) was stirred at room temperature for 18 hrs. The solvent was evaporated off and the residue was dissolved in water (20 ml) and extracted with dichloromethane (20 ml). This organic layer was discarded. The aqueous layer was then acidified with concentrated HCl and extracted with dichloromethane (3×20 ml). The combined organic layers were dried over magnesium sulfate and concentrated to give a colorless oil (1.9 g, 72%). 1H NMR (300 MHz, methanol-d4) δ 4.17 (m, 2H), 1.89 (m, 4H), 1.25 (m, 3H), 0.83 (m, 6H). ES-LCMS m/z 188 (M+H).

Provenance & Evidence