p-Toluenesulfonic acid → Dodecyl beta-D-Glucofuranosiduron-6,3-Lactone

Participants

Reaction Conditions

Reaction Steps

20 g of Glucurono-6,3-lactone (0.11 mole), 0.2 g p-toluenesulfonic acid (1.05×10-3 mole) and 164.0 g of dodecanol (0.88 mole) were placed in a three-necked flask equipped with a mechanical stirrer, thermometer and short path distillation head. The mixture was heated to 110° C. until D-glucurono-6,3-lactone dissolved. The reaction mixture was neutralized with 1 ml of 1N methanolic KOH at 25° C., filtered over silica and washed with methanol. A vacuum was applied to remove the methanol and dodecanol yielding a syrup. Hexane was added and dodecyl β-D-glucofuranosidurono-6,3-lactone crystallized selectively. The yield was 15.9 g (42%). The product was recrystallized from hexane/ether mixture. MP 88°-89° C. (99.9% pure).

Provenance & Evidence