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 Chapter 21: Ester Enolates 
Ch 21 contents
Malonic Ester Synthesis
acetoacetic ester synthesis
Reaction type :Nucleophilic substitution, then ester hydrolysis and finally decarboxylation (!)

Summary

malonic acid
Related Reactions
 OVERVIEW OF MALONIC ESTER SYNTHESIS
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 malonic ester synthesis of carboxylic acids
Step 2:
Acid or base catalysed hydrolysis of both esters  to give the parent dicarboxylic acid, a substituted malonic acid.
Step 3:
Loss of CO2 = decarboxylation, readily occurs giving a substituted carboxylic acid.
Mechanisms for the individual steps can be found on the linked pages.


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