Sodium Chloride → HCID 18600187, compound

HRID 1583571Notes

Reaction equation

HRID 1583571 reaction equation
[CH2:1]([O:17][C:18]1[C@@H:23]([C@H:24]([CH2:26][OH:27])[OH:25])[O:22][C:20](=[O:21])[C:19]=1[OH:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[H-].[Na+].[CH2:31](Cl)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[Na+]>CN(C=O)C>[CH2:31]([O:28][C:19]1[C:20]([O:22][C@H:23]([C@H:24]([CH2:26][OH:27])[OH:25])[C:18]=1[O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:21])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 148434423-O-Cetyl ascorbic acid

Product 1

HCID 18600187HCID 18600187, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
90 °C

Procedure

A solution of 0.933 g. of 3-O-n-hexadecyl-L-ascorbic acid in 7.5 ml. of anhydrous DMF was added slowly at ambient temperature under a nitrogen atmosphere to a suspension of 2.45 millimoles of NaH in 10 ml. of anhydrous DMF in a 50 ml., 3-neck round-bottom flask equipped with magnetic stirrer, drying tube and dropping funnel. The reaction mixture was stirred for 25 minutes (until H2 evolution stopped) at which time the sodium salt (on the 2-hydroxy) of 3-O-n-hexadecyl-L-ascorbic acid had formed. A solution of 0.295 g. of benzyl chloride in 2 ml. of anhydrous DMF was added. The reaction mixture was stirred at ambient temperature for about 50 minutes. The reaction temperature was then raised to 90° C., at which temperature stirring was continued for an additional 50 minutes. The reaction mixture was cooled and saturated aqueous sodium chloride (brine) added. The resulting aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine and dried. The dried extract was decolorized with charcoal, filtered and the volatile constituents removed in vacuo. The resulting yellow syrup was chromatographed over silica gel 60 using 1:9 ethyl acetate-toluene as the eluant. Fractions shown by TLC to contain the desired product were combined and the solvent removed therefrom. 694 mg. (62% yield) of a yellow waxy solid comprising purified 2-O-benzyl-3-O-n-hexadecyl-L-ascorbic acid were obtained.

Workup

  1. custom, 3-neck round-bottom flask equipped with magnetic stirrer
  2. customdrying tube
  3. customhad formed
  4. stirringThe reaction mixture was stirred at ambient temperature for about 50 minutes
  5. stirringstirring
  6. waitwas continued for an additional 50 minutes
  7. temperatureThe reaction mixture was cooled
  8. extractionThe resulting aqueous mixture was extracted with ethyl acetate
  9. extractionThe ethyl acetate extract
  10. washwas washed with brine
  11. customdried
  12. extractionThe dried extract
  13. filtrationfiltered
  14. customthe volatile constituents removed in vacuo
  15. customThe resulting yellow syrup was chromatographed over silica gel 60 using 1:9 ethyl acetate-toluene as the eluant
  16. customthe solvent removed
  17. custom(62% yield) of a yellow waxy solid comprising purified 2-O-benzyl-3-O-n-hexadecyl-L-ascorbic acid
  18. customwere obtained

Sources & evidence

ORD record
ord-907af02ad2fb44d5ad557720a1e00636
Source dataset
uspto-grants-1985_11
Patent number
US04552888

Reaction notes

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