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Dimedone

Dimedone

5,5-dimethyl-1,3-cyclohexanedione, Dimethyldihydroresorcinol, Methone

Dimedone is an organic compound with the formula . Classified as a cyclic diketone, it is a derivative of 1,3-cyclohexanedione. It is a white solid that is soluble in water, as well as ethanol and methanol. It once was used as a reagent to test for the aldehyde functional group.

Synthesis

Dimedone is prepared from mesityl oxide and diethyl malonate via a Michael addition reaction.

Chemical properties

Tautomerism

Dimedone is in equilibrium with its tautomer in solution — in a 2:1 keto to enol ratio in chloroform.

Diagram of tautomeric equilibrium of dimedone

Crystalline dimedone contains chains of molecules, in the enol form, linked by hydrogen bonds:

Ball-and-stick model of a hydrogen-bonded dimedone chain, as found in the crystal structure

Reaction with aldehydes

Dimedone reacts with aldehydes to give crystalline derivatives, whose melting points can be used to distinguish between aldehydes.

:[[File:Fällung dimedon.tif|549x549px|Reaction of dimedone with formaldehyde]]

References

References

  1. R. L. Shriner and H. R. Todd. (1935). "5,5-dimethyl-1,3-cyclohexanedione". Organic Syntheses.
  2. "Dimedone synthesis".
  3. {{Clayden
  4. M. Bolte and M. Scholtyssik. (October 1997). "Dimedone at 133K". Acta Crystallogr. C.
  5. (1946). "Methone Derivatives of Aldehydes". The Journal of Organic Chemistry.
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diketones 3-hydroxypropenals
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