Dimedone

Quality 0.50 · 2 views · Updated 2 months ago

title: "Dimedone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["diketones", "3-hydroxypropenals"] topic_path: "general/diketones" source: "https://en.wikipedia.org/wiki/Dimedone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 401997177 | ImageFileL1 =dimedone.png | ImageFileR1 =Dimedone-3D-balls.png | PIN =5,5-Dimethylcyclohexane-1,3-dione | OtherNames =Cyclomethone, 5,5-dimethyl-1,3-cyclohexanedione, Dimethyldihydroresorcinol, Methone |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 29091 | InChI = 1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 | InChIKey = BADXJIPKFRBFOT-UHFFFAOYAX | StdInChI_Ref = | StdInChI = 1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 | StdInChIKey_Ref = | StdInChIKey = BADXJIPKFRBFOT-UHFFFAOYSA-N | CASNo_Ref = | CASNo =126-81-8 | UNII_Ref = | UNII = B2B5DSX2FC | PubChem =31358 | SMILES = O=C1CC(=O)CC(C)(C)C1 |Section2={{Chembox Properties | C=8|H=12|O=2 | MolarMass = | Appearance =White solid | Density = | MeltingPtC = 147 to 150 | MeltingPt_notes = (decomposes) | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Dimedone is an organic compound with the formula . 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.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/0/0e/Dimedone-tautomerism-2D-skeletal.png" caption="Diagram of tautomeric equilibrium of dimedone"] ::

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

::figure[src="https://upload.wikimedia.org/wikipedia/commons/3/36/Dimedone-hydrogen-bonded-chain-from-xtal-3D-balls.png" caption="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.

:[[File:Fällung dimedon.tif|549x549px|Reaction of dimedone with formaldehyde]]

References

References

  1. R. L. Shriner and H. R. Todd. (1935). "5,5-dimethyl-1,3-cyclohexanedione". Organic Syntheses.
  2. "Dimedone synthesis".
  3. {{Clayden
  4. M. Bolte and M. Scholtyssik. (October 1997). "Dimedone at 133K". Acta Crystallogr. C.
  5. (1946). "Methone Derivatives of Aldehydes". The Journal of Organic Chemistry.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

diketones3-hydroxypropenals