Acetone → (+)-5,6-O-Isopropylidene-L-ascorbic acid

HRID 359138Notes

Reaction equation

HRID 359138 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[O:10]=[C:11]1[O:17][C@H:16]([C@H:18]([CH2:20][OH:21])[OH:19])[C:14]([OH:15])=[C:12]1[OH:13].[CH3:22][C:23]([CH3:25])=O>>[CH3:22][C:23]1([CH3:25])[O:19][C@H:18]([C@H:16]2[O:17][C:11](=[O:10])[C:12]([OH:13])=[C:14]2[OH:15])[CH2:20][O:21]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 24681Fuming sulfuric acidHCID 54670067L-Ascorbic Acid

Product 1

HCID 54691418(+)-5,6-O-Isopropylidene-L-ascorbic acid

Conditions

Temperature
0 °C

Procedure

55 g of 24% strength oleum were added dropwise to 480 ml of acetone (water content about 1.4%) at -10° C. 120 g of L-ascorbic acid were introduced into the resulting mixture at about 0° C., and the reaction mixture was stirred for 6 h at 0° C. It was then cooled to -15° C. and the crystals formed were filtered off under suction. The resulting filter cake was pressed dry, washed with twice 100 ml of ice cold acetone and dried at room temperature under reduced pressure from a water pump.

Workup

  1. temperatureIt was then cooled to -15° C.
  2. customthe crystals formed
  3. filtrationwere filtered off under suction
  4. filtrationThe resulting filter cake
  5. customwas pressed dry
  6. washwashed with twice 100 ml of ice cold acetone
  7. dry with materialdried at room temperature under reduced pressure from a water pump

Sources & evidence

ORD record
ord-ccdb06c00ac8426383d7680d5434eb69
Source dataset
uspto-grants-1991_03
Patent number
US04999437

Reaction notes

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