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.

Dimedone

Names
Preferred IUPAC name 5,5-Dimethylcyclohexane-1,3-dione
Other names Cyclomethone, 5,5-dimethyl-1,3-cyclohexanedione, Dimethyldihydroresorcinol, Methone
Identifiers
CAS Number	126-81-8 Y
3D model (JSmol)	Interactive image
ChemSpider	29091 Y
ECHA InfoCard	100.004.369
PubChem CID	31358
UNII	B2B5DSX2FC Y
CompTox Dashboard (EPA)	DTXSID8021987
InChI InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 Y Key: BADXJIPKFRBFOT-UHFFFAOYSA-N Y InChI=1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 Key: BADXJIPKFRBFOT-UHFFFAOYAX
SMILES O=C1CC(=O)CC(C)(C)C1
Properties
Chemical formula	C8H12O2
Molar mass	140.182 g·mol−1
Appearance	White solid
Melting point	147 to 150 °C (297 to 302 °F; 420 to 423 K) (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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]

Crystalline dimedone contains chains of molecules, in the enol form, linked by hydrogen bonds:^[4]

Reaction with aldehydes

Dimedone reacts with aldehydes to give crystalline derivatives, whose melting points can be used to distinguish between aldehydes.^[5]