2-Furanone

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2-Furanone
Furan-2-one.png
Names
IUPAC name
5H-furan-2-one
Other names
furan-2-one, γ-crotonolactone, butenolide
Identifiers
CAS number497-23-4 YesY
ChEBICHEBI:38118 YesY
ChEMBLChEMBL166223 YesY
ChemSpider9917 YesY
Jmol-3D imagesImage
KEGGC17601 YesY
MeSHbutenolide
PubChem10341
Properties
C4H4O2
Molar mass84.07336
Density1.185 g/cm3, liquid
Melting point4 °C (39 °F; 277 K)[1]
Boiling point86 °C (187 °F; 359 K) 12 mm Hg[1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references
 
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2-Furanone
Furan-2-one.png
Names
IUPAC name
5H-furan-2-one
Other names
furan-2-one, γ-crotonolactone, butenolide
Identifiers
CAS number497-23-4 YesY
ChEBICHEBI:38118 YesY
ChEMBLChEMBL166223 YesY
ChemSpider9917 YesY
Jmol-3D imagesImage
KEGGC17601 YesY
MeSHbutenolide
PubChem10341
Properties
C4H4O2
Molar mass84.07336
Density1.185 g/cm3, liquid
Melting point4 °C (39 °F; 277 K)[1]
Boiling point86 °C (187 °F; 359 K) 12 mm Hg[1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

2-Furanone, also known as γ-crotonolactone (GCL), is a heterocyclic organic compound. Classified as a lactone, this colourless liquid is colloquially called "butenolide." As a class of compounds, substituted derivatives, which are not in fact prepared from the parent 2-furanone, are called butenolides.

Synthesis and reactions[edit]

2-Furanone is prepared by oxidation of furfural:[2]

Oxidation of furfural to furanone.png

It exists in equilibrium with the tautomer 2-hydroxyfuran, which serves as an intermediate in the interconversion between the β- and α-furanones. The β form is the more stable. The interconversion is catalyzed by base.

2-Furanones can be converted to furans by a two-step process of reduction followed by dehydration. First the carbon-oxygen double bond is reduced by trimethylsilylation of the oxygen centre.

See also[edit]

References[edit]

  1. ^ a b Sigma-Aldrich Chemicals Product detail
  2. ^ Jan H. Näsman (1993). "3-Methyl-2(5H)-furanone". Org. Synth. ; Coll. Vol. 1, p. 396