Acetone → Diacetone L-sorbose

HRID 358137

Reaction equation

HRID 358137 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].IN1[C:18](=O)[CH2:17][CH2:16]C1=O.[CH3:21][C:22]([CH3:24])=O>>[CH3:21][C:22]1([CH3:24])[O:6][C@H:5]2[C@@H:7]3[O:8][C:17]([CH3:18])([CH3:16])[O:10][C@:9]3([CH2:11][OH:12])[O:4][C@H:3]2[CH2:2][O:1]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 6904L-(-)-SorboseHCID 120273N-Iodosuccinimide

Product 1

HCID 11043496Diacetone L-sorboseYield 58.4%

Conditions

Temperature
60 °C

Procedure

To 200 ml of acetone were added 10.0 g of L-sorbose and 225 mg of N-iodosuccinimide and the mixture was refluxed with stirring in a water bath at 60° C. for 6 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 8.43 g (58.4%) of 2,3:4,6-di-O-isopropylidene-L-sorbofuranose (purity ≥97%).

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-e9eb00c953be4be9ae291df8ab30e400
Source dataset
uspto-grants-1984_08
Patent number
US04464530

Linked notes

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