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Dimedone is a cyclic diketone used in organic chemistry to determine whether a compound contains an aldehyde group. Cyclohexanediones in general can be used as catalysts in the formation of transition-metal complexes. Other uses include applications in colorimetry, crystallography, luminescence and spectrophotometric analysis. It can also be used for chemistry involving organic compounds of low electrical resistance.
Synthesis
Dimedone is prepared from mesityl oxide and diethyl malonate.Physical properties
Dimedone usually comes in the form of white crystals. It is stable under ambient conditions and soluble in water, as well as ethanol andmethanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
. It has a melting point range of 147–150 °C (420–423 K).
Chemical properties
Tautomerism
Dimedone is in equilibrium with its tautomer in solution — in a 2:1 keto to enol ratio inchloroform
Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
.
Crystalline dimedone contains chains of molecules, in the enol form, linked by hydrogen bond
In chemistry, a hydrogen bond (or H-bond) is a primarily electrostatic force of attraction between a hydrogen (H) atom which is covalently bound to a more electronegative "donor" atom or group (Dn), and another electronegative atom bearing a ...
s:
Reaction with aldehydes
Dimedone reacts with aldehydes to give crystalline derivatives, whose melting points can be used to distinguish between aldehydes. :References
{{reflist Diketones 3-Hydroxypropenals