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

HRID 444063

Reaction equation

HRID 444063 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)-glycerolYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.056 g. of 50 wt. % mineral oil dispersion, 22 mmoles) was added to a solution of 1,2-di-O-(n-hexadecyl)-glycerol (9.73 g., 18 mmoles) in tetrahydrofuran (150 ml.) and the resulting solution stirred for 20 minutes at room temperature under nitrogen. m-Cyanobenzyl bromide (4.0 g., 20 mmoles) was added and the reaction mixture stirred overnight at room temperature under nitrogen. Water (200 ml.) was then added cautiously and the resulting mixture extracted with ethyl acetate (3×150 ml.). The combined ethyl acetate extract was dried (MgSO4), filtered and evaporated in vacuo to an oil (12 g.), which was purified by silica gel chromatography (elution with benzene:hexane) [8.0 g., 68% yield, oil, ir (CHCl3) 2230 cm-1 ].

Workup

  1. stirringthe reaction mixture stirred overnight at room temperature under nitrogen
  2. extractionthe resulting mixture extracted with ethyl acetate (3×150 ml.)
  3. extractionThe combined ethyl acetate extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil (12 g.), which
  7. customwas purified by silica gel chromatography (elution with benzene:hexane) [8.0 g., 68% yield, oil, ir (CHCl3) 2230 cm-1 ]

Sources & evidence

ORD record
ord-d0d52e488d75449eaa6c34ec73bff122
Source dataset
uspto-grants-1981_04
Patent number
US04262021

Linked notes

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