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2-Furanone is a heterocyclic organic compound. It is also known as γ-crotonolactone (GCL), as it is formally the lactone derived from γ-hydroxy isocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for the butenolide class of compounds. It is a colourless liquid.
It exists in equilibrium with the tautomer 2-hydroxy
Synthesis and reactions
2-Furanone is prepared by oxidation offurfural
Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs ...
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It exists in equilibrium with the tautomer 2-hydroxyfuran
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.
Furan is a colorless, flammable, highly ...
, 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 furan
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.
Furan is a colorless, flammable, highly ...
s by a two-step process of reduction followed by dehydration.
See also
* :Furanones, various substituted structural analogs * Pyrone, which has one more carbon atom in the ringReferences
{{DEFAULTSORT:Furanone, 2- Furanones GHB receptor ligands