Water → Allylmalonic acid
Reaction equation
[OH-].[K+].O.C([O:7][C:8](=[O:17])[C:9]([CH2:15][CH3:16])(CC)[C:10]([O-:12])=[O:11])C=C.[CH3:18]CCCCCC>>[CH2:15]([CH:9]([C:8]([OH:7])=[O:17])[C:10]([OH:12])=[O:11])[CH:16]=[CH2:18]Participants
5
Procedure
Potassium hydroxide (15.6 g, 0.28 mol), 15 ml of distilled water and 50 ml of heptane are added to a round bottom flask. Allyldiethylmalonate (22.0 g, 1.1 mol) is added slowly to the reaction mixture with stirring and refluxed for sufficient time to complete hydrolysis. Ethanol is removed with a rotoevaporator. The resultant product is cooled in a beaker and acidified with sulfuric acid. The final solution is extracted with diethylether. The ether layer is collected, dried over MgSO4, and ether is removed with a rotoevaporator. The crude allylmalonic acid is crystalized from petroleum ether.