:5-Hydroxy-2(5H)-furanone
{{DISPLAYTITLE:5-Hydroxy-2(5H)-furanone}}
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| Name = 5-Hydroxy-2(5H)-furanone
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| ImageFile = 5-Hydroxy-2(5H)-furanone.svg
| ImageSize = 175px
| ImageName = 5-Hydroxy-2(5H)-furanone
| PIN = 5-Hydroxyfuran-2(5H)-one
| OtherNames = 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
| Section1 = {{Chembox Identifiers
| ChEBI_Ref =
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| SMILES = C1=CC(=O)OC1O
| ChemSpiderID_Ref =
| ChemSpiderID = 19821
| PubChem = 21076
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| StdInChI = InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-3,5H
| StdInChIKey_Ref =
| StdInChIKey = DUAZKLYNTLDKQK-UHFFFAOYSA-N
| CASNo = 14032-66-7
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| Section2 = {{Chembox Properties
| C=4 | H=4 | O=3
| Appearance =
| Density = 1.503 g/mL
| MeltingPt = 55 °C
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| Section3 = {{Chembox Hazards
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5-Hydroxy-2(5H)-furanone is a furanone derived from oxidation of furfural using singlet oxygen.{{cite journal|last1=Hoydonckx|first1=H. E.|last2=Rhijn|first2=W. M. Van|last3=Rhijn|first3=W. Van|last4=De Vos|first4=D. E.|last5=Jacobs|first5=P. A.|title=Furfural and Derivatives|journal=Ullmann's Encyclopedia of Industrial Chemistry|page=5|doi=10.1002/14356007.a12_119.pub2|year=2007|isbn=978-3527306732}}{{cite book|last1=Zeitsch|first1=K.J.|title=The Chemistry and Technology of Furfural and its Many By-Products (Sugar Series)|date=2000|publisher=Elsevier Science|isbn=9780444503510|pages=170–171|edition=1st|url=https://books.google.com/books?id=HWkCqDDlUt0C&dq=2-Hydroxyfuranone-%285%29+rose+bengal&pg=PA170}} 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.{{cite journal|last1=Fariña|first1=Francisco|last2=Martín|first2=M. Rosario|last3=Martín|first3=Victoria|last4=de Guereñu|first4=Ana Martínez|title=Cycloaddition of Nitrile Oxides to 4-Oxobut-2-enoic Acid Derivatives|journal=Heterocycles|date=1994|volume=38|issue=6|pages=1307–1316|doi=10.3987/COM-94-6679|doi-access=free}}{{cite journal|last1=L. Feringa|first1=Ben|last2=de Lange|first2=Ben|last3=Kok|first3=Johan|last4=S. Faber|first4=Wijnand|title=Catalytic kinetic resolution of 5-alkoxy-2(5H)-furanones|journal=Tetrahedron|date=1994|volume=50|issue=16|pages=4775–4794|doi=10.1016/S0040-4020(01)85016-X}}
Chemical properties
5-Hydroxy-2(5H)-furanone exists in chemical equilibrium with its isomer, cis-β-formylacrylic acid, in ring-chain tautomerism:{{cite journal|last1=Poskonin|first1=V. V.|last2=Badovskaya|first2=L. A.|title=Unusual Conversion of 5-Hydroxy-2(5H)furanone in Aqueous Solution|journal=Chemistry of Heterocyclic Compounds|date=2003|volume=39|issue=5|pages=594–597|doi=10.1023/A:1025137914137|s2cid=98418207}}
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.
See also
References
{{DEFAULTSORT:Hydroxy-2(5H)-furanone, 5-}}