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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

Additional recommended knowledge

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

References

  1. ^ Smith, Janice Gorzynski. Organic Chemistry: Second Ed. 2008. pp 905-906
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Acetoacetic_ester_synthesis". A list of authors is available in Wikipedia.
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