J. Seydel, E. R. Garrett, W. Diller
Jul 1, 1967
Citations
0
Influential Citations
20
Citations
Journal
Journal of pharmaceutical sciences
Abstract
5-Methyl-3 (2H)-furanone (VIII) is produced from 2-deoxy-D-ribose (I) under defined conditions of acid, temperature, and time, Its production is a direct function of sugar concentration and its ultraviolet absorbance serves as a sensitive assay for the sugar. The compound VIII was identified by spectral data (NMR, U.V., I.R.), thin-layer chromatography R f values in three different solvent systems, and chemical reactivities. The compound VIII obtained from deoxyribose and synthesized by a different route was the same. A mechanism dependent on the direction of water elimination after cyclization, dehydration, and rehydration can explain the formation of VIII and the previously obtained levulinic acid whose production from furfuryl alcohol (III) was explained by a similar mechanism. The spectrally observed kinetic intermediate with a λ max. at 225 mμ is consistent with the proposed mechanism.