Dimedone

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.
Image:Dimedone-tautomerism-2D-skeletal.png|300px|Diagram of tautomeric equilibrium of dimedone
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.