2-Furanone

2-Furanone

Names
IUPAC name 5H-furan-2-one
Other names furan-2-one, γ-crotonolactone, butenolide
Identifiers
CAS Number	497-23-4 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:38118 Y
ChEMBL	ChEMBL166223 Y
ChemSpider	9917 Y
ECHA InfoCard	100.007.128
KEGG	C17601 Y
MeSH	butenolide
PubChem	10341
InChI InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 Y Key: VIHAEDVKXSOUAT-UHFFFAOYSA-N Y InChI=1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 Key: VIHAEDVKXSOUAT-UHFFFAOYAD
SMILES O=C\1OC/C=C/1
Properties
Chemical formula	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

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

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

• 5-hydroxy-2(5H)-furanone
• pyrone slightly larger

References