Dimedone

Dimedone

Error creating thumbnail: Error creating thumbnail:
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 checkY
3D model (JSmol)	Interactive image
ChemSpider	29091 checkY
ECHA InfoCard
E number
PubChem CID	31358
UNII	B2B5DSX2FC checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 checkY Key: BADXJIPKFRBFOT-UHFFFAOYSA-N checkY 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). checkY verify (what is checkY☒N ?) Infobox references

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.

Chemical properties

Tautomerism

Dimedone is in equilibrium with its tautomer in solution — in a 2:1 keto to enol ratio in chloroform.

Diagram of tautomeric equilibrium of dimedone

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

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.

Reaction of dimedone with formaldehyde