1,2-O-dioleyl-3-O-tritylglycerol → 2,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanol

HRID 376411

Reaction equation

HRID 376411 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([CH2:41][O:42]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>ClC(Cl)(Cl)C(O)=O.C(Cl)Cl>[CH2:1]([O:19][CH2:20][CH:21]([CH2:41][OH:42])[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 1

HCID 702527781,2-O-dioleyl-3-O-tritylglycerol

Product 1

HCID 53803432,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanolYield 87%

Reagents, catalysts & solvents 1

HCID 19349592Trichloroacetic acid methylene chlorideSolvent

Procedure

1,2-O-Dioleyl-3-O-tritylglycerol (6.10 g, 7.3 mmol) was reacted with 5% trichloroacetic acid/methylene chloride (50 ml, w/v) at ambient temperature for 1 hour. The organic layer was then washed with saturated aqueous sodium hydrogen carbonate solution and water, dried, and concentrated. The residue was purified by column chromatography (silica gel/chloroform) to provide 3.75 g (87%) of the title compound.

Workup

  1. washThe organic layer was then washed with saturated aqueous sodium hydrogen carbonate solution and water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (silica gel/chloroform)

Sources & evidence

ORD record
ord-b38c504bdc664d459a5be7f3ddc76782
Source dataset
uspto-grants-2000_02
Patent number
US06020317

Linked notes

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