Acetoacetic ester synthesis

Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis.

CH₃COCH₂COOCH₂CH₃ + R-X → CH₃COCH₂-R

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Mechanism

A strong base deprotonates the dicarbonyl α-carbon. This carbon is preferred over the methyl carbon because the formed enolate is conjugated, and thus resonance stabilized. The carbon then undergoes nucleophilic substitution. When heated with aqueous acid, the newly alkylated ester is hydrolyzed to a β-keto acid, which is decarboxylated to form a methyl ketone.^[1]

See also

• Malonic ester synthesis

References

1. ^ Smith, Janice Gorzynski. Organic Chemistry: Second Ed. 2008. pp 905-906