Tetrahydrofuran → Furfural

Participants

Reaction Steps

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.

Provenance & Evidence