CH3COCH2COOEt

CH3COCH2COOEt is commonly known as ethyl acetoacetate. Its IUPAC name is ethyl 3-oxobutanoate, and it is a beta-keto ester with the molecular framework CH3-CO-CH2-COOEt. The molecule contains two carbonyl groups (a ketone and an ester) separated by a methylene, giving it an active methylene that can be deprotonated to form enolates.

Ethyl acetoacetate is a versatile building block in organic synthesis. The acidic methylene hydrogen enables alkylation at the C-3 position after enolate formation, allowing the construction of a range of 1,3-dicarbonyl compounds. It participates in reactions such as Claisen condensations, Robinson annulations, and various Michael-type additions, and it serves as a precursor to heterocycles and various medicinally relevant molecules. Its beta-keto ester functionality makes it useful for downstream transformations leading to dyes, agrochemicals, and pharmaceuticals.

Preparation of ethyl acetoacetate typically involves esterification of acetoacetic acid with ethanol in the presence of an acid catalyst (a Fischer esterification approach) or other routes that introduce the ethyl ester onto the acetoacetate framework. It is commercially available as a colorless to pale liquid and is often stored under appropriate conditions to minimize hydrolysis.

Safety and handling require standard precautions for flammable, irritant organic liquids. Use in a well-ventilated area, avoid inhalation and skin contact, and store away from heat and oxidizers.