Acetone → Diacetone L-sorbose

HRID 1462582Notes

Reaction equation

HRID 1462582 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].O[CH2:6][C:7]([C@H:9]([C@@H:11]([C@H:13]([CH2:15][OH:16])[OH:14])[OH:12])[OH:10])=[O:8].Cl.[C:18](=O)([O-])O.[Na+].O1[CH2:28][CH2:27]OCC1>>[CH3:1][C:2]1([CH3:4])[O:10][C@H:9]2[C@@H:11]3[O:12][C:27]([CH3:28])([CH3:18])[O:14][C@:13]3([CH2:15][OH:16])[O:8][C@H:7]2[CH2:6][O:3]1

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6904L-(-)-SorboseHCID 312751,4-DioxaneHCID 516892Sodium Bicarbonate

Product 1

HCID 11043496Diacetone L-sorboseYield 78.9%

Conditions

Temperature
60 °C

Procedure

To 200 ml of acetone were added 10.0 g of L-sorbose, 200 mg of cupric acetate monohydrate and 1 ml of a 2 mole/l solution of hydrogen chloride in dioxane, and the mixture was stirred for 7 hours under reflux in a warm-water bath at 60° C. The refluxing solvent was continuously dried with 20 g of molecular sieves 3A which was placed between the reaction vessel and the cooling tube. After the conclusion of the reaction, a small amount of aqueous sodium hydrogencarbonate was added to the reaction mixture, and the acetone was distilled off under reduced pressure. The residue was dissolved in benzene, and the solution was washed with aqueous sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. When the benzene was distilled off under reduced pressure, there was obtained 11.4 g (78.9%) of 2,3:4,6-di-O-isopropylidene-L-sorbofuranose as a residue. The compound, when recrystallized from petroleum ether, showed a melting point of 77° to 78° C.

Workup

  1. temperatureunder reflux in
  2. dry with materialThe refluxing solvent was continuously dried with 20 g of molecular sieves 3A which
  3. customAfter the conclusion of the reaction
  4. distillationthe acetone was distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in benzene
  6. washthe solution was washed with aqueous sodium hydrogencarbonate and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationWhen the benzene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0852c8c07c824505b2a949f0663b50f9
Source dataset
uspto-grants-1984_07
Patent number
US04460767

Reaction notes

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