Water → 1,2-Di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol

HRID 46507

Reaction equation

HRID 46507 reaction equation
[H-].[Na+].[CH2:3]([O:19][CH2:20][CH:21]([CH2:39][OH:40])[O: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][CH2:36][CH2:37][CH3:38])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:41]([C:43]1[CH:44]=[C:45]([CH:48]=[CH:49][CH:50]=1)[CH2:46]Br)#[N:42].O>O1CCCC1>[CH2:3]([O:19][CH2:20][CH:21]([CH2:39][O:40][CH2:46][C:45]1[CH:48]=[CH:49][CH:50]=[C:43]([C:41]#[N:42])[CH:44]=1)[O: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][CH2:36][CH2:37][CH3:38])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 1025482,3-Bis(hexadecyloxy)propan-1-ol

Product 1

HCID 234661581,2-Di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (50% mineral oil dispersion; 1.056 g, 0.022 mole) was added to a solution of 1,2-di-O-n-hexadecyl glycerol in tetrahydrofuran (150 ml) and stirred for 20 minutes under nitrogen. m-Cyanobenzylbromide (4.0 g, 0.020 mole) was added to the mixture and allowed to react to room temperature overnight. Water (200 ml) and then cautiously added and the aqueous mixture extracted with ethyl acetate (3×150 ml). The extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give an oil (12 g), which was chromatographed on silica gel (eluted with benzene/hexane, 8/2) resulting in pure 1,2-Di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol (8.0 g): oil; ir(CHCl3) 2230 cm-1.

Workup

  1. customto react to room temperature overnight
  2. extractionthe aqueous mixture extracted with ethyl acetate (3×150 ml)
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da18f997aed546d095abbeb7e881e89a
Source dataset
uspto-grants-1979_11
Patent number
US04173641

Linked notes

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