5-Hydroxy-2(5H)-furanone

5-Hydroxy-2(5H)-furanone

Names
IUPAC name 5-Hydroxy-2(5H)-furanone
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
CAS Number	14032-66-7
3D model (Jmol)	Interactive image
ChemSpider	19821
ECHA InfoCard	100.112.891
PubChem	21076
InChI InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-3,5H Key: DUAZKLYNTLDKQK-UHFFFAOYSA-N
SMILES C1=CC(=O)OC1O
Properties
Chemical formula	C4H4O3
Molar mass	100.07 g·mol−1
Density	1.503 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5-Hydroxy-2(5H)-furanone is a furanone derived from oxidation of furfural using singlet oxygen.^[1][2]

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]

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

• Butenolide
• Tetronic acid

References

1. 1 2 Hoydonckx, H. E.; Rhijn, W. M. Van; Rhijn, W. Van; De Vos, D. E.; Jacobs, P. A. "Furfural and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry: 5. doi:10.1002/14356007.a12_119.pub2. 
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. 
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". 50 (16): 4775–4794. doi:10.1016/S0040-4020(01)85016-X. 
5. 1 2 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.