|Chapter 21: Ester Enolates|
|OVERVIEW OF ACETOACETIC ESTER SYNTHESIS|
First, an acid-base reaction. Ethoxide functions as a base and removes the acidic a-hydrogen giving the reactive enolate which is then alkylated.
Acid or base catalysed hydrolysis of the ester to the parent carboxylic acid.
Loss of CO2 = decarboxylation, readily occurs giving a substituted ketone.
|Mechanisms for the individual steps can be found on the linked pages.|
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|