2-Furanone

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2-Furanone
Skeletal formula of 2-furanone
Ball-and-stick model of the 2-furanone molecule
Names
IUPAC name
5H-furan-2-one
Other names
furan-2-one, γ-crotonolactone, butenolide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.128
KEGG
MeSH butenolide
Properties
C4H4O2
Molar mass 84.07336
Density 1.185 g/cm3, liquid
Melting point 4 to 5 °C (39 to 41 °F; 277 to 278 K)[1]
Boiling point 86 to 87 °C (187 to 189 °F; 359 to 360 K) 12 mm Hg[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. ^ Näsman, Jan H. (1990). "3-Methyl-2(5H)-furanone". Organic Syntheses. 68: 162. doi:10.15227/orgsyn.068.0162.