Misplaced Pages

Dimedone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.369 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3Key: BADXJIPKFRBFOT-UHFFFAOYSA-N
  • InChI=1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3Key: BADXJIPKFRBFOT-UHFFFAOYAX
SMILES
  • O=C1CC(=O)CC(C)(C)C1
Properties
Chemical formula C8H12O2
Molar mass 140.182 g·mol
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

References

  1. R. L. Shriner and H. R. Todd (1935). "5,5-dimethyl-1,3-cyclohexanedione". Organic Syntheses. 15: 16. doi:10.1002/0471264180.os015.06. ISBN 0471264229.
  2. "Dimedone synthesis". ChemTube3D. Retrieved 11 May 2023.
  3. Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 530. ISBN 978-0-19-850346-0.
  4. M. Bolte and M. Scholtyssik (October 1997). "Dimedone at 133K". Acta Crystallogr. C. 53 (10): IUC9700013. Bibcode:1997AcCrC..53C0013B. doi:10.1107/S0108270197099423.
  5. Horning, E. C.; Horning, M. G. (1946). "Methone Derivatives of Aldehydes". The Journal of Organic Chemistry. 11 (1): 95–99. doi:10.1021/jo01171a014. ISSN 0022-3263. PMID 21013441.
Categories: