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. Derivatives of dimedone and 1,3-cyclohexanedione derivatives are used as reagents for selective detection of sulfenic acids in biological samples.

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.

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

Reaction with aldehydes

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

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