Methanol → 1,2-di-O-(n-hexadecyl)-3-O-(3-formylbenzyl)-glycerol

HRID 1701601Notes

Reaction equation

HRID 1701601 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([C:46]#N)[CH: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].[H-].C([Al+]CC(C)C)C(C)C.C[OH:59].[H-]>C1C=CC=CC=1.O>[CH2:1]([O:17][CH2:18][CH:19]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH:46]=[O:59])[CH: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

7

Reactant 4

HCID 887MethanolHCID 166653HydrideHCID 21225700DiisobutylaluminumhydrideHCID 234661581,2-Di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol

Product 1

HCID 234661481,2-di-O-(n-hexadecyl)-3-O-(3-formylbenzyl)-glycerolYield 40%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A solution of 1,2-di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol (5.0 g., 7.6 mmoles) and diisobutylaluminum hydride (1.17 g., 8.2 mmoles) in benzene (25 ml.) was stirred for 16 hours at ambient temperature. The reaction mixture was treated with methanol (4.22 ml.) and water (2.5 ml.) and stirred to decompose unreacted hydride, and then filtered and extracted with benzene (3×25 ml.). The combined benzene extract was dried (Na2SO4), filtered and evaporated in vacuo to an oil, which was purified by silica gel chromatography (elution with benzene) [2.0 g., 40% yield, oil, ir (CHCl3) 1700 cm-1, n.m.r. (CDCl3) δ 10.1 (s, 1, --ArCHO)].

Workup

  1. filtrationfiltered
  2. extractionextracted with benzene (3×25 ml.)
  3. extractionThe combined benzene extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil, which
  7. customwas purified by silica gel chromatography (elution with benzene) [2.0 g., 40% yield, oil, ir (CHCl3) 1700 cm-1, n.m.r. (CDCl3) δ 10.1 (s, 1, --ArCHO)]

Sources & evidence

ORD record
ord-a12694b864104a3d80e9346c7218e0a7
Source dataset
uspto-grants-1980_03
Patent number
US04193999

Reaction notes

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