Methanol → methyl b-D-glucofuranosidurono-6,3-lactone

Participants

Reaction Steps

D-Glucurono-6,3-lactone (100.0 g, 0.57 mole), anhydrous methanol (200.0 g, 6.24 moles), and methanesulfonic acid (3 drops) were placed in an oven dried three-necked round bottom flask equipped with mechanical stirrer, thermometer and condenser. The mixture was heated for 24 hours at reflux, cooled and neutralized with 0.1N methanolic KOH. The mixture was filtered and washed with cold methanol (20 ml) yielding 20.9 g of methyl b-D-glucofuranosidurono-6,3-lactone (MbGlucl). By further concentration of the filtrate an additional 28.2 g of MbGlucl was isolated giving a total yield of 49.1 g (45.3%), MP=139° C., purity=99.1% (GC).

Provenance & Evidence