m-Chloroperbenzoic acid → 1,2-Di-O-(n-hexadecyl)-3-O-(2,3-epoxypropyl)-glycerol

HRID 1701598Notes

Reaction equation

HRID 1701598 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:37][O:38][CH2:39][CH:40]=[CH2:41])[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[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].ClC1C=CC=C(C(OO)=[O:50])C=1.S(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:1]([O:17][CH2:18][CH:19]([CH2:37][O:38][CH2:39][CH:40]1[O:50][CH2:41]1)[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[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

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 234661031,2-di-O-(n-hexadecyl)-3-allyl-glycerolHCID 23665763Sodium Bisulfite

Product 1

HCID 234661141,2-Di-O-(n-hexadecyl)-3-O-(2,3-epoxypropyl)-glycerolYield 82%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1,2-di-O-(n-hexadecyl)-3-allyl-glycerol (5.8 g., 10.0 mmoles) and m-chloroperbenzoic acid (1.86 g., 10.8 mmoles) in benzene (50 ml.) was stirred at reflux for 16 hours. The reaction mixture was then cooled, treated with saturated aqueous sodium bisulfite solution (10 ml.) and saturated aqueous sodium bicarbonate solution (50 ml.), and extracted with ether (3×50 ml.). The combined ether extract was washed with water (100 ml.), washed with saturated aqueous sodium chloride solution (100 ml.), dried (MgSO4), filtered and evaporated in vacuo to an oil (4.9 g., 82% yield, olefinic protons absent by n.m.r. analysis), which was purified by silica gel chromatography (elution with benzene:ethyl acetate) (4.2 g., 70% yield, oil-solidified on standing).

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with ether (3×50 ml.)
  4. extractionThe combined ether extract
  5. washwas washed with water (100 ml.)
  6. washwashed with saturated aqueous sodium chloride solution (100 ml.)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo to an oil (4.9 g., 82% yield, olefinic protons absent by n.m.r. analysis), which
  10. customwas purified by silica gel chromatography (elution with benzene:ethyl acetate) (4.2 g., 70% yield, oil-solidified on standing)

Sources & evidence

ORD record
ord-8ce08193c3494014894cf3f2445edeb7
Source dataset
uspto-grants-1980_03
Patent number
US04193999

Reaction notes

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