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

HRID 1440945Notes

Reaction equation

HRID 1440945 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]1[O:12][C:10](=[O:11])[C@@H:8]([OH:9])[C@H:6]1[OH:7])[OH:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>>[O:11]([CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24])[C@@H:10]1[O:12][C@@H:5]2[C@@H:3]([C:2]([O:7][C@@H:6]2[C@H:8]1[OH:9])=[O:1])[OH:4]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 81931-DodecanolHCID 92283Glucuronolactone

Product 1

HCID 11035338Dodecyl beta-D-Glucofuranosiduron-6,3-Lactone

Conditions

Temperature
110 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a8e97311b370426ebb3b6ad23a92be75
Source dataset
uspto-grants-1996_03
Patent number
US05501812

Reaction notes

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