Acetoacetic ester synthesis

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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.

Acetoacetic ester synthesis

Mechanism[edit]

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][2]

Acetoacetic ester mechanism.png

See also[edit]

References[edit]

  1. ^ Smith, Janice Gorzynski. Organic Chemistry: Second Ed. 2008. pp 905–906
  2. ^ Acetoacetic Ester Synthesis – Alkylation of Enolates | PharmaXChange.info