Dimedone
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Dimedone is an organic compound with the formula Template:Chem2. 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.[1][2]
Chemical properties
Tautomerism
Dimedone is in equilibrium with its tautomer in solution — in a 2:1 keto to enol ratio in chloroform.[3]
Diagram of tautomeric equilibrium of dimedone
Crystalline dimedone contains chains of molecules, in the enol form, linked by hydrogen bonds:[4]
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.[5]
References
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