Sulfuric Acid → Diacetone-D-glucose

HRID 462336

Reaction equation

HRID 462336 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].S(=O)(=O)(O)O>CC(C)=O>[CH3:2][C:3]1([CH3:5])[O:4][C@@H:3]([C@H:5]2[O:6][C@@H:11]3[O:12][C:9]([CH3:11])([CH3:7])[O:10][C@@H:9]3[C@H:7]2[OH:8])[CH2:2][O:1]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 7067560Diacetone-D-glucose

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In this example, 125 g of powdered D-glucose is added to a stirred solution of 120 ml of concentrated 96 wt.% sulfuric acid in 3 liters of acetone and the mixture is stirred vigorously at room temperature overnight. The reaction mixture is cooled to 10° C. and gaseous ammonia is bubbled keeping the temperature below 25° C. Solids are filtered off and the filtrate is concentrated under reduced pressure. The residue is treated with 1 liter of water and extracted three times with 300 ml of methylene chloride. The methylene chloride extracts are combined, washed with water, dried with annydrous magnesium sulfate, and concentrated to give a white crystalline residue of crude 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose.

Workup

  1. temperatureThe reaction mixture is cooled to 10° C.
  2. customgaseous ammonia is bubbled
  3. customthe temperature below 25° C
  4. filtrationSolids are filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. additionThe residue is treated with 1 liter of water
  7. extractionextracted three times with 300 ml of methylene chloride
  8. washwashed with water
  9. dry with materialdried with annydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f877d429d1764acba378f6c74ffa9b3b
Source dataset
uspto-grants-1985_05
Patent number
US04515618

Linked notes

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