Sulfuric Acid → 1,4-Anhydrohexitol

Participants

Reaction Steps

This was prepared by modification of the method of S. Soltzberg (J. Am. Chem. Soc., 68, 919 (1946)). In a 2L round bottom flask, D-Sorbitol (130 g) was added to a solution of 1.43 g of concentrated H2SO4 in 19.5 ml of H2O. The flask was warmed in a 100° oil bath until the solid began to melt. The flask was then evacuated, maintained at approximately 20-25 mm Hg, and placed in a 140° oil bath. The reaction was stirred at 125°-145° for 30 minutes at reduced pressure. The reaction flask was then cooled to room temperature and 500 ml of H2O and approximately 25 g of Norit were added. The flask was warmed in a 80° oil bath for several minutes and the mixture was filtered. After cooling to room temperature, the filtrate was neutralized with barium acetate to pH 6.5, and allowed to stand for one hour. The precipitate was then removed by filtration and the solvent was removed to provide a colorless, oily solid. Chromatography on silica gel (750 g 0-30% CH3OH in CHCl3) yielded 30.0 g of impure [2R-2α(S*),3α,4β]]-tetrahydro-β,3,4-trihydroxy-2-furanethanol, which was used as such in the following step.

Provenance & Evidence