Acetic Acid → HCID 25155178, compound

HRID 410139Notes

Reaction equation

HRID 410139 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:29][OH:30])[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([OH:28])CO)[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].C(O)(=O)C>C(O)(C)C.O.C(O)C.C[N+](CC(NN)=O)(C)C.[Cl-]>[CH2:1]([O:17][CH2:18][CH:19]([CH2:29][OH:30])[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[O: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]

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 25155177HCID 25155177, compound

Product 1

HCID 25155178HCID 25155178, compoundYield 27%

Reagents, catalysts & solvents 4

HCID 67156Betaine Hydrazide HydrochlorideCatalystHCID 702EthanolSolventHCID 962WaterSolvent3×HCID 3776IsopropanolSolvent

Procedure

As depicted in Scheme III, 1-Hexadecyl-2-(5′,6′-dihydroxy-hexanyl)-glycerol (7.84 grams) was dissolved in isopropanol (50 ml) and water (12 ml). NaIO4 (9 grams) was added and the reaction mixture was stirred at room temperature for 3 hours. Water (50 ml) was added and the reaction mixture extracted with chloroform (3×50 ml). dried over anhydrous Na2SO4, filtered and the solvent removed under to reduced pressure yielding 5.56 grams. The crude product was dissolved in ethanol (60 ml) and glacial acetic acid (2.3 grams). Girard's reagent T (5.6 grams) was added and the reaction mixture was refluxed for 2 hours. The reaction mixture was cooled in ice-bath, alkaline solution (2.3 grams in 45 ml water) was added and the mixture was extracted with ether (3×25 ml). The etheral phase was washed with water and the water combined with the alkaline phase. The aqueous phase was acidified with concentrated HCl (4.4 ml) and extracted with ether (3×25 ml). Washing with water, saturated aqueous sodium bicarbonate (3×25 ml), water (2×25 ml). drying over anhydrous Na2SO4 and removal of the solvent under reduced pressure gave 1.95 grams (0.0049 mol) of 1-Hexadecyl-2-(5′-oxo-pentanyl)-glycerol (26.9% yield).

Workup

  1. extractionthe reaction mixture extracted with chloroform (3×50 ml)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed under to reduced pressure
  5. customyielding 5.56 grams
  6. temperaturethe reaction mixture was refluxed for 2 hours
  7. temperatureThe reaction mixture was cooled in ice-bath
  8. extractionthe mixture was extracted with ether (3×25 ml)
  9. washThe etheral phase was washed with water
  10. extractionextracted with ether (3×25 ml)
  11. washWashing with water, saturated aqueous sodium bicarbonate (3×25 ml), water (2×25 ml)
  12. dry with materialdrying over anhydrous Na2SO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b06865bbc1e04301a2228a0fa8e64a81
Source dataset
uspto-grants-2014_06
Patent number
US08759557B2

Reaction notes

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