Oxygen → 2,5-Dimethyl-4-hydroxy-tetrahydrofuran-3-one

HRID 1578017Notes

Reaction equation

HRID 1578017 reaction equation
[CH3:1][CH:2]1[CH:6]([OH:7])[CH:5]([OH:8])[CH:4]([CH3:9])[O:3]1.O=O>[Ag].[Cu]>[CH3:1][CH:2]1[C:6](=[O:7])[CH:5]([OH:8])[CH:4]([CH3:9])[O:3]1

Participants

5

Reactant 2

HCID 977OxygenHCID 204869562,5-Dimethyl-3,4-dihydroxy-tetrahydrofuran

Product 1

HCID 103131462,5-Dimethyl-4-hydroxy-tetrahydrofuran-3-one

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 23978CopperCatalyst

Procedure

2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one is prepared by first epoxidizing hex-3-ene-2,5-diol in the liquid phase with hydrogen peroxide to give the novel compound 3,4-epoxy-hexane-2,5-diol, which at 40°-280° C. is converted, by means of a catalytic amount of an acid, to the novel compound 2,5-dimethyl-3,4-dihydroxy-tetrahydro-furan. The latter is dehydrogenated by means of oxygen over a silver catalyst or copper catalyst to give the nove compound 2,5-dimethyl-4-hydroxy-tetrahydrofuran-3-one, which is oxidized by means of bismuth oxide, in concentrated acetic acid solution, to give the desired compound 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one.

Sources & evidence

ORD record
ord-b09a9443421c457c95337c00953f202f
Source dataset
uspto-grants-1981_09
Patent number
US04290960

Reaction notes

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