反应详情

温度

110 °C

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).

1. customequipped with a mechanical stirrer
2. distillationthermometer and short path distillation head
3. dissolutiondissolved
4. customwas neutralized with 1 ml of 1N methanolic KOH at 25° C.
5. filtrationfiltered over silica
6. washwashed with methanol
7. customto remove the methanol and dodecanol yielding a syrup
8. additionHexane was added
9. customdodecyl β-D-glucofuranosidurono-6,3-lactone crystallized selectively
10. customThe product was recrystallized from hexane/ether mixture