Iodine → Diacetone L-sorbose

HRID 358141Notes

Reaction equation

HRID 358141 reaction equation
[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4].I.II>CC(C)=O>[CH3:2][C:3]1([CH3:5])[O:6][C@H:5]2[C@@H:7]3[O:8][C:9]([CH3:11])([CH3:7])[O:10][C@:9]3([CH2:11][OH:12])[O:4][C@H:3]2[CH2:2][O:1]1

Participants

5

Reactant 3

HCID 807IodineHCID 6904L-(-)-SorboseHCID 24841Hydrogen iodide

Product 1

HCID 11043496Diacetone L-sorboseYield 167.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To 200 ml of acetone were added 10.0 g of L-sorbose, 90 mg of hydriodic acid (57%) and 50.8 mg of iodine and the mixture was refluxed with stirring in a water bath at 60° C. for 8 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. The reaction mixture was then subjected to an after-treatment similar to that described in Example 11 to give 12.07 g (83.6%) of 2,3:4,6-di-O-isopropylidene-L-sorbofuranose (purity ≥98%).

Workup

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A

Sources & evidence

ORD record
ord-aa28db81cf7d473c9a5b092a3b890c2a
Source dataset
uspto-grants-1984_08
Patent number
US04464530

Reaction notes

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