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

HRID 724756

Reaction equation

HRID 724756 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-c1a07edf93274ff392e5f0ec1c77a155
Source dataset
uspto-grants-1998_01
Patent number
US05705188

Linked notes

Loading…