CH3COCH2COOR

CH3COCH2COOR, also known as an alkyl acetoacetate or a beta-keto ester, is an organic compound characterized by a ketone functional group adjacent to an ester functional group, separated by a methylene group. The R group represents an alkyl or aryl substituent. This structural arrangement imparts specific chemical properties and reactivity to the molecule.

The presence of the alpha-methylene group, located between the carbonyl groups, makes the hydrogen atoms attached to it relatively acidic. This acidity allows for facile deprotonation by a base, generating a resonance-stabilized enolate anion. This enolate anion is a versatile nucleophile and can participate in various important organic reactions, such as alkylation and acylation, making it a key intermediate in organic synthesis.

Alkyl acetoacetates are commonly synthesized through the Claisen condensation of ethyl acetate or similar esters. They are valuable building blocks in the synthesis of a wide range of organic molecules, including heterocyclic compounds, pharmaceuticals, and flavors. For instance, they are crucial in the Knorr pyrrole synthesis and the Hantzsch pyridine synthesis. The specific properties and applications of CH3COCH2COOR depend on the nature of the R group in the ester moiety.