Dimedone

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 ;
3D model (JSmol)	Interactive image;
ChemSpider	29091 ;
ECHA InfoCard	100.004.369
PubChem CID	31358;
UNII	B2B5DSX2FC ;
CompTox Dashboard (EPA)	DTXSID8021987 ;
	InChI InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 Key: BADXJIPKFRBFOT-UHFFFAOYSA-N ; 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). verify (what is ?) 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.^[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]

References

^ 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.
^ "Dimedone synthesis". ChemTube3D. Retrieved 11 May 2023.
^ Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 530. ISBN 978-0-19-850346-0.
^ M. Bolte and M. Scholtyssik (October 1997). "Dimedone at 133K". Acta Crystallogr. C. 53 (10): IUC9700013. Bibcode:1997AcCrC..53C0013B. doi:10.1107/S0108270197099423.
^ 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.

[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.

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