diethylmalonate

Diethyl malonate is an organic compound with the chemical formula CH2(COOCH2CH3)2. It is a diester of malonic acid and is a colorless liquid with a faint fruity odor. Diethyl malonate is soluble in ethanol and ether but has limited solubility in water. It is commonly prepared through the esterification of malonic acid with ethanol in the presence of an acid catalyst.

This compound is a versatile building block in organic synthesis, particularly in the synthesis of pharmaceuticals, fragrances, and flavors. Its most notable use is in the malonic ester synthesis, a method for alkylating active methylene compounds. In this reaction, the acidic protons on the carbon atom between the two ester groups can be removed by a base, forming a carbanion that can then react with alkyl halides. Subsequent hydrolysis and decarboxylation of the substituted malonate yield a substituted acetic acid. This process is crucial for creating a wide range of carboxylic acids with varying alkyl chains.

Diethyl malonate is also used in the synthesis of barbiturates, a class of drugs used for their sedative and hypnotic effects. It finds applications in the production of vitamins, such as vitamin B1, and in the synthesis of certain polymers and agricultural chemicals. Due to its reactivity and diverse applications, diethyl malonate remains an important reagent in both laboratory and industrial organic chemistry.