Chemical Properties
Ethyl 4-chloroacetoacetate is colorless to pale reddish-yellow clear liquid
Uses
Ethyl-4-chloracetoacetate (CAAEt) is used as intermediate for organic syntheses, e.g. ethyl 4-chloro-3-arylaminocrotonates, diethyl succinylsuccinate, 2-alkyl-4-hydroxy-6-chloromethylpyrimidines, 4- chloromethylcoumarines. Product Data Sheet
Uses
Ethyl 4-chloroacetoacetate is used as a precursor in the preparation of phosphorous ylides. It finds application in regular film coating, pharmaceutical coating and formulation.
Preparation
Preparative Methods of Ethyl 4-chloroacetoacetate: the industrial production of the esters is made exclusively by chlorination of diketene
followed by reaction of the intermediate acid chloride with the corresponding alcohol.
[2]
Solubility in organics
Ethyl 4-Chloroacetoacetate is is soluble in most organic solvents. The ethyl ester (1a) is 12% enolized in the pure liquid, and highly
enolized (60% in CCl4) in nonpolar solvents.
[1]
storage
Ethyl 4-chloroacetoacetate is lachrymators of moderate toxicity; uses in a fume
hood.
References
1. Rappoport, Z. The Chemistry of Enols; Wiley: New York, 1990; p 365.
2. Lonza AG; U.S. Patent 4 473 508, 1984 (CA 1985, 102, 5715).
