Acetic Acid → HCID 25155178, compound

HRID 1645449Notes

Reaction equation

HRID 1645449 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 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 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-861f82589c814a2199edf999ac0452a0
Source dataset
uspto-grants-2012_02
Patent number
US08124800B2

Reaction notes

Loading…