Sulfuric Acid → Furaneol

HRID 1764489Notes

Reaction equation

HRID 1764489 reaction equation
[O:1]=[C:2]1[CH:6]([CH3:7])[O:5][CH:4]([CH3:8])[C:3]1=NO.[OH:11]S(O)(=O)=O>>[O:1]=[C:2]1[CH:6]([CH3:7])[O:5][C:4]([CH3:8])=[C:3]1[OH:11]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 713696984-Oxo-3-oximino-2,5-dimethyl-tetrahydrofuran

Product 1

HCID 19309Furaneol

Procedure

10 g of 4-oxo-3-oximino-2,5-dimethyl-tetrahydrofuran and 50 ml of 10% strength H2SO4 are heated at 80° C and the hydrolysis is followed by thin layer chromatography. The oxime has been converted after 3 hours. In its place, 4-oxo-3-hydroxy-2,5-dimethyl-4,5-dihydrofuran has been formed, as established by isolating the product and comparing the chromatographic and spectroscopic data with those of a comparative substance.

Sources & evidence

ORD record
ord-88eec9296a30460ca19f6decade2825f
Source dataset
uspto-grants-1978_09
Patent number
US04116982

Reaction notes

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