1-O-Hexadecylglycerol → 1-(Hexadecyloxy)-3-((4-methoxyphenyl)diphenylmethoxy)-2-propanol

HRID 1639331Notes

Reaction equation

HRID 1639331 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([OH:22])[CH2:20][OH:21])[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].[CH3:23][O:24][C:25]1[CH:44]=[CH:43][C:28]([C:29](Cl)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:27][CH:26]=1>N1C=CC=CC=1.O1CCCC1>[CH2:1]([O:17][CH2:18][CH:19]([OH:22])[CH2:20][O:21][C:29]([C:28]1[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=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]

Participants

5

Reactant 2

HCID 727331-O-HexadecylglycerolHCID 84462p-(Chlorodiphenylmethyl)anisole

Product 1

HCID 142607721-(Hexadecyloxy)-3-((4-methoxyphenyl)diphenylmethoxy)-2-propanolYield 13.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 84.5 g of 3-(hexadecyloxy)-1,2-propanediol in 265 ml of dry pyridine, stirred in an ice bath under nitrogen, was added in a steady stream a solution of 115.5 g of 4-methoxytrityl chloride in 150 ml of dry tetrahydrofuran. This mixture was stirred in the ice bath for 30 minutes, then at room temperature for 2 hours, then refrigerated at 0° C. overnight. The mixture was concentrated to remove the volatile solvents. The residual solution was dissolved in 400 ml of chloroform, washed twice with 200 ml portions of 10% aqueous sodium bicarbonate and twice with 200 ml portions of water, dried and evaporated. The residue was evaporated twice from toluene, taken up in ether, chilled and filtered. The filtrate was taken to dryness, giving a syrup. A 30 g portion of this syrup was dissolved in petroleum ether and chromatographed on a silica gel column eluting with 20% ether in petroleum ether. The product fractions 6-20 (200 ml each) were combined and evaporated, giving 21 g of the desired compound.

Workup

  1. waitrefrigerated at 0° C. overnight
  2. concentrationThe mixture was concentrated
  3. customto remove the volatile solvents
  4. dissolutionThe residual solution was dissolved in 400 ml of chloroform
  5. washwashed twice with 200 ml portions of 10% aqueous sodium bicarbonate and twice with 200 ml portions of water
  6. customdried
  7. customevaporated
  8. customThe residue was evaporated twice from toluene
  9. temperaturechilled
  10. filtrationfiltered
  11. customgiving a syrup
  12. customchromatographed on a silica gel column
  13. washeluting with 20% ether in petroleum ether
  14. customevaporated

Sources & evidence

ORD record
ord-98a2a8b138a249dc817fc0e8999656c7
Source dataset
uspto-grants-1989_11
Patent number
US04883816

Reaction notes

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