5-Hydroxy-2(5H)-furanone explained

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.

Uses

5-Hydroxy-2(5H)-furanone is a potent pesticide 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. 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. 10.1002/14356007.a12_119.pub2. 2007. 978-3527306732.
2. Book: Zeitsch. K.J.. The Chemistry and Technology of Furfural and its Many By-Products (Sugar Series). 2000. Elsevier Science. 9780444503510. 170–171. 1st.
3. Fariña. Francisco. Martín. M. Rosario. Martín. Victoria. de Guereñu. Ana Martínez. Cycloaddition of Nitrile Oxides to 4-Oxobut-2-enoic Acid Derivatives. Heterocycles. 1994. 38. 6. 1307–1316. 10.3987/COM-94-6679. free.
4. L. Feringa. Ben. de Lange. Ben. Kok. Johan. S. Faber. Wijnand. Catalytic kinetic resolution of 5-alkoxy-2(5H)-furanones. Tetrahedron. 1994. 50. 16. 4775–4794. 10.1016/S0040-4020(01)85016-X.
5. Poskonin. V. V.. Badovskaya. L. A.. Unusual Conversion of 5-Hydroxy-2(5H)furanone in Aqueous Solution. Chemistry of Heterocyclic Compounds. 2003. 39. 5. 594–597. 10.1023/A:1025137914137. 98418207.