Tetrahydrofuran → Furfural

HRID 1165749Notes

Reaction equation

HRID 1165749 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([CH:10]1[C:15](=[O:16])[CH:14]=[C:13]([CH3:17])[O:12][C:11]1=[O:18])=[O:9].[O:19]1CCCC1>>[CH3:17][C:13]1[O:12][C:11](=[O:18])[CH:10]([C:8]([CH3:7])=[O:9])[C:15](=[O:16])[CH:14]=1.[CH:6](=[O:19])[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 703631753-(2-furylacryloyl)-6-methyl-2H-pyran-2,4(3H)-dione

Product 2

HCID 7362FurfuralHCID 122903Dehydroacetic acid

Procedure

In 270 ml of tetrahydrofuran was dissolved 32.0 g of 3-(2-furylacryloyl)-6-methyl-2H-pyran-2,4(3H)-dione which had been obtained by condensation between dehydroacetic acid and furfural. To the solution, 1.6 g of 5% palladium on carbon was added as the hydrogenation catalyst. Hydrogenation was carried out at room temperature under a pressure of 5 kg/cm2 for 10 hours. The catalyst was removed by filtration and the solvent was evaporated under a reduced pressure. The light-yellow oily product thus obtained was purified by silica gel chromatography to obtain a 21.0 g (yield: 65%) of 3-(3-(2-tetrahydrofuryl)propionyl)-6-methyltetrahydropyran-2,4-dione in the form of the light-yellow crystal, m.p. 43°-45° C.

Sources & evidence

ORD record
ord-5245b5c5cea3463bbe95f4325a12d6b9
Source dataset
uspto-grants-1990_03
Patent number
US04912100

Reaction notes

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