Malonic ester synthesis



The malonic ester synthesis is a chemical reaction where acetic acid.[1]

Mechanism

A strong base is required to deprotonate the center proton. The protons alpha to synthon.

The esters chosen are usually the same as the base used, i.e. ethyl esters with sodium ethoxide. This is to prevent scrambling by transesterification.

Variations

Dialkylation

The ester may be dialkylated if deprotonation and alkylation are repeated before the addition of aqueous acid.

Cycloalkylcarboxylic acid synthesis

Intramolecular malonic ester synthesis occurs when reacted with a dihalide.[3]

See also

References

  1. ^ House, Herbert O. (1972). Modern Synthetic Reactions. Menlo Park, CA.: W. A. Benjamin. ISBN 0-8053-4501-9. 
  2. ^ Malonic Ester Synthesis. Organic Chemistry Portal. Retrieved on 2007-10-26.
  3. ^ Smith, Janice Gorzynski. Organic Chemistry: Second Ed. 2008. pp 905-906
 
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