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Acetoacetic Ester Synthesis
acetoacetic ester synthesis
Reaction type : Nucleophilic substitution, then ester hydrolysis and finally decarboxylation (!)


Related Reactions
Step 1:
First, an acid-base reaction. Ethoxide functions as a base and removes the acidic a-hydrogen giving the reactive enolate which is then alkylated.
steps in the acetoacetic ester synthesis of ketones
Step 2:
Acid or base catalysed hydrolysis of the ester to the parent carboxylic acid.
Step 3:
Loss of CO2 = decarboxylation, readily occurs giving a substituted ketone.
Mechanisms for the individual steps can be found on the linked pages.

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organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary