Chemistry:5-Hydroxy-2(5H)-furanone

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5-Hydroxy-2(5H)-furanone
5-Hydroxy-2(5H)-furanone
Names
Preferred IUPAC name
5-Hydroxyfuran-2(5H)-one
Other names
5-Hydroxy-5H-furan-2-one, 2-Hydroxyfuranone-(5), β-oxo-γ-butyrolactone, 4-Oxobut-2-enoic acid, 2,5-dihydrofuran-2-one, beta-Formylacrylic acid lactol, 2-Oxo-5-hydroxy-2,5-dihydrofuran, 2-Hydroxy-2,5-dihydro-5-furanone, 5-Hydroxy-2,5-dihydrofuran-2-one; γ-Hydroxybutenolide
Identifiers
3D model (JSmol)
ChemSpider
Properties
C4H4O3
Molar mass 100.073 g·mol−1
Density 1.503 g/mL
Melting point 55 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

5-Hydroxy-2(5H)-furanone is a furanone derived from oxidation of furfural using singlet oxygen.[1][2] This oxidation is carried out generally in methanol or ethanol with a sensitizer like methylene blue or Rose bengal. The mechanism of this reaction is depicted as below.

Furfural-oxidation.png


Uses

5-Hydroxy-2(5H)-furanone is a potent pesticide[1] and a four carbon building block for various heterocycles.[3][4]

Chemical properties

5-Hydroxy-2(5H)-furanone exists in chemical equilibrium with its isomer, cis-β-formylacrylic acid, in ring-chain tautomerism:[5]

Tautomer of 5-Hydroxy-2(5H)-furanone.PNG

Under some conditions the compound will isomerize into succinic anhydride. Upon heating in strongly basic solution (pH > 9) this isomer will hydrate to succinic acid.[5]

See also

References

  1. ↑ 1.0 1.1 Hoydonckx, H. E.; Rhijn, W. M. Van; Rhijn, W. Van; De Vos, D. E.; Jacobs, P. A. (2007). "Furfural and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry: 5. doi:10.1002/14356007.a12_119.pub2. ISBN 978-3527306732. 
  2. ↑ Zeitsch, K.J. (2000). The Chemistry and Technology of Furfural and its Many By-Products (Sugar Series) (1st ed.). Elsevier Science. pp. 170–171. ISBN 9780444503510. https://books.google.com/books?id=HWkCqDDlUt0C&dq=2-Hydroxyfuranone-%285%29+rose+bengal&pg=PA170. 
  3. ↑ Fariña, Francisco; Martín, M. Rosario; Martín, Victoria; de Guereñu, Ana Martínez (1994). "Cycloaddition of Nitrile Oxides to 4-Oxobut-2-enoic Acid Derivatives". Heterocycles 38 (6): 1307–1316. doi:10.3987/COM-94-6679. 
  4. ↑ L. Feringa, Ben; de Lange, Ben; Kok, Johan; S. Faber, Wijnand (1994). "Catalytic kinetic resolution of 5-alkoxy-2(5H)-furanones". Tetrahedron 50 (16): 4775–4794. doi:10.1016/S0040-4020(01)85016-X. 
  5. ↑ 5.0 5.1 Poskonin, V. V.; Badovskaya, L. A. (2003). "Unusual Conversion of 5-Hydroxy-2(5H)furanone in Aqueous Solution". Chemistry of Heterocyclic Compounds 39 (5): 594–597. doi:10.1023/A:1025137914137. 



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