Bismuth-oxygen → Furaneol

HRID 1578018Notes

Reaction equation

HRID 1578018 reaction equation
[CH3:1][CH:2]1[C:6](=[O:7])[CH:5]([OH:8])[CH:4]([CH3:9])[O:3]1.[Bi]=O>C(O)(=O)C>[CH3:9][CH:4]1[C:5](=[O:8])[C:6]([OH:7])=[C:2]([CH3:1])[O:3]1

Participants

4

Reactant 2

HCID 6327914Bismuth-oxygenHCID 103131462,5-Dimethyl-4-hydroxy-tetrahydrofuran-3-one

Product 1

HCID 19309Furaneol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

the resulting 2,5-dimethyl-4-hydroxy-tetrahydrofuran-3-one is oxidized with bismuth oxide, in concentrated acetic acid solution, to give 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one.

Sources & evidence

ORD record
ord-c3d20c2578404fd4a0ad83e19c49e08b
Source dataset
uspto-grants-1981_09
Patent number
US04290960

Reaction notes

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