Sulfuric Acid → Diacetone-D-glucose

HRID 2296383Notes

Reaction equation

HRID 2296383 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 anhydrous magnesium sulfate, and concentrated to give a white crystalline residue of crude 1,2:5,6-di-O-isopropylidene-a-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 anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0342e12d95684852af2743778f98d523
Source dataset
uspto-grants-1984_01
Patent number
US04429119

Reaction notes

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