1-Bromooctane → Glyceryl octyl ascorbic acid

HRID 1698289Notes

Reaction equation

HRID 1698289 reaction equation
[CH2:1]([O:6][C:7]1[C@@H:12]([C@H:13]([CH2:15][OH:16])[OH:14])[O:11][C:9](=[O:10])[C:8]=1[OH:17])[CH:2]([CH2:4][OH:5])[OH:3].C(=O)([O-])O.[Na+].[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CS(C)=O>[CH2:1]([O:6][C:7]1[C@@H:12]([C@H:13]([CH2:15][OH:16])[OH:14])[O:11][C:9](=[O:10])[C:8]=1[O:17][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:2]([CH2:4][OH:5])[OH:3]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 516892Sodium BicarbonateHCID 672677953-Glyceryl ascorbate

Product 1

HCID 54588053Glyceryl octyl ascorbic acidYield 61.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under an argon atmosphere, 3-O-glyceryl ascorbic acid (54.1 g) obtained in Example 1 was stirred in DMSO (200 mL), and further, sodium hydrogen carbonate (18.5 g) was added and the mixture was stirred at room temperature for 30 minutes. Thereafter, octyl bromide (63.7 g) was added and the mixture was heated up to 100° C. and stirred for 3 hours, followed by extraction with ethyl acetate. Then, the extracted liquid was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and 131 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:10/3/0.4), and concentration was performed under reduced pressure to obtain 3-O-glyceryl-2-O-octyl ascorbic acid (48.0 g).

Workup

  1. temperaturethe mixture was heated up to 100° C.
  2. stirringstirred for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the extracted liquid was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure, and 131 g of the resultant residue
  6. washElution
  7. concentrationwas performed with chloroform/methanol/water(volume ratio:10/3/0.4), and concentration

Sources & evidence

ORD record
ord-bb3b254aa44549898d5e82008234d856
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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