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2-Furanone
2-Furanone is a heterocyclic organic compound. It is also known as γ-crotonolactone (GCL), as it is formally the lactone derived from γ-hydroxyisocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for the butenolide class of compounds. It is a colourless liquid.
Synthesis and reactions
2-Furanone is prepared by oxidation of furfural:
:[[File:Synthesis 2-Furanone.svg|400px]]
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 reaction.
Furanone is thought to contribute to the unique taste of maple syrup.
References
References
- Sigma-Aldrich Chemicals [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/283754 Product detail]
- (1990). "3-Methyl-2(5''H'')-furanone". Organic Syntheses.
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