Sorbitol → (3S)-2-(1,2-dihydroxyethyl)oxolane-3,4-diol

HRID 1934857Notes

Reaction equation

HRID 1934857 reaction equation
[OH:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])O)[OH:4]>O>[CH2:11]1[O:12][CH:5]([CH:3]([OH:4])[CH2:2][OH:1])[C@@H:7]([OH:8])[CH:9]1[OH:10]

Participants

3

Reactant 1

HCID 5780Sorbitol

Product 1

HCID 103023(3S)-2-(1,2-dihydroxyethyl)oxolane-3,4-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

To 680.0 grams of meadowfoam acid is added to the sorbitol intermediate. Next add 0.1% stannous oxylate based upon the total weight of the batch after all ingredients have been charged, under agitation. The temperature of the mass is raised to 180-200° C. and water is stripped off as formed. The acid value and hydroxyl value drop to vanishingly small values, and the saponification value increases to theoretical.

Workup

  1. additionhave been charged, under agitation
  2. customas formed
  3. temperaturethe saponification value increases to theoretical

Sources & evidence

ORD record
ord-82920f04735c448bbcc0ad5b1399c705
Source dataset
uspto-grants-2002_05
Patent number
US06384248B1

Reaction notes

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