Water → 2-O-(2,3-Dihydroxypropyl)-L-ascorbic acid

HRID 1698285Notes

Reaction equation

HRID 1698285 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].C(=O)([O-])O.[Na+].O.[CH2:19]1[O:21][CH:20]1[CH2:22][OH:23]>CO>[CH2:19]([O:4][C:3]1[C:2]([O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]=1[OH:6])=[O:1])[CH:20]([CH2:22][OH:23])[OH:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11164GlycidolHCID 516892Sodium BicarbonateHCID 54670067L-Ascorbic Acid

Product 1

HCID 672668142-O-(2,3-Dihydroxypropyl)-L-ascorbic acidYield 8.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Under an argon atmosphere, L-ascorbic acid (10.0 g) and sodium hydrogen carbonate (9.54 g) were added to water and the resultant mixture was stirred at room temperature for 30 minutes, then, glycidol (8.41 g) was added thereto. Thereafter, the mixture was heated up to 60° C. and stirred for 5 hours. Thereto, methanol was added and filtration was performed. The filtrate was concentrated under reduced pressure, and 19.0 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:6/4/1), and concentration was performed under reduced pressure to obtain 2-O-glyceryl ascorbic acid (1.21 g).

Workup

  1. filtrationfiltration
  2. concentrationThe filtrate was concentrated under reduced pressure, and 19.0 g of the resultant residue
  3. washElution
  4. concentrationwas performed with chloroform/methanol/water(volume ratio:6/4/1), and concentration

Sources & evidence

ORD record
ord-76d2d5cfcf5b44c689fa87f722c2bb9c
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

Loading…