Dimedone

Dimedone is an organic compound with the formula (CH3)2C(CH2)2(CO)2(CH2). 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.

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.


 * Fällung dimedon.tif