Potassium Carbonate → L-Ascorbic Acid

HRID 505069Notes

Reaction equation

HRID 505069 reaction equation
C(O[C@@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1[O:24][C:25]1[C:26]([O:28][C@H:29]([C@H:32]([CH2:34][OH:35])[OH:33])[C:30]=1[OH:31])=[O:27])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[O:27]=[C:26]1[O:28][C@H:29]([C@H:32]([CH2:34][OH:35])[OH:33])[C:30]([OH:31])=[C:25]1[OH:24]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 546818862-o-(2,3,4,6-Tetra-o-acetyl-beta-d-glucopyranosyl)ascorbic acid

Product 1

HCID 54670067L-Ascorbic AcidYield 179.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)ascorbic acid (300 mg, 0.6 mmol) was dissolved in methanol (10 ml), and to the solution was added a solution in which potassium carbonate (600 mg) had been dissolved in water (9 ml). The mixture was stirred for 30 minutes. The reaction solution was neutralized with AMBERLITE® IR-120 (H+), and filtered to remove the resin. The filtrate was washed successively with methanol and 50% aqueous methanol solution. The filtrate and the washing solution were combined, and concentrated, and then water was added thereto, followed by freeze-drying to obtain 2-O-β-D-glucopyranosyl)ascorbic acid as amorphous crystals (190 mg, yield: 100%). PMR (δ ppm, D2O); 3.1-3.3 (4H, m), 3.4-3.5 (3H, m), 3.58(1H d) , 3.80(1H, t), 4.61(1H, d), 4.66(1H, d). FABMS(−) m/z: 337.

Workup

  1. filtrationfiltered
  2. customto remove the resin
  3. washThe filtrate was washed successively with methanol and 50% aqueous methanol solution
  4. concentrationconcentrated
  5. additionwater was added
  6. customby freeze-drying

Sources & evidence

ORD record
ord-8792d5e72a7645eb9cabb1d5681e4639
Source dataset
uspto-grants-2010_08
Patent number
US07781409B2

Reaction notes

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