Methyl iodide → 1,1',1''-{[(2-Methoxyoctadecyl)oxy]methanetriyl}tribenzene

HRID 638531Notes

Reaction equation

HRID 638531 reaction equation
[H-].[Na+].[C:3]([O:22][CH2:23][CH:24]([OH:41])[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][CH2:38][CH2:39][CH3:40])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:42]I>O1CCCC1>[C:3]([O:22][CH2:23][CH:24]([O:41][CH3:42])[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][CH2:38][CH2:39][CH3:40])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 104369742-Octadecanol, 1-(triphenylmethoxy)-

Product 1

HCID 539210951,1',1''-{[(2-Methoxyoctadecyl)oxy]methanetriyl}tribenzeneYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of sodium hydride (2.40 g, 60% oil dispersion, washed with dry petroleum ether) in dry tetrahydrofuran (40 ml) was portionwise added (rac)-1-O-trityl-1,2-octadecanediol (12.2 g) at ambient temperature. After the mixture was stirred for 30 minutes at the same temperature, a solution of methyl iodide (13.1 g) in dry tetrahydrofuran (40 ml) was dropwise added during a period of 45 minutes. After stirring for 3.5 hours at the same temperature, the mixture was evaporated under reduced pressure. The residue was dissolved in a mixture of diethyl ether and 0.5N aqueous sulfuric acid. The separated organic layer was dried and evaporated under reduced pressure. The residue was triturated in petroleum ether to remove impurities by filtration. The filtrate was evaporated to yield 9.8 g of (rac)-1-O-trityl-2-O-methyl-1,2-octadecanediol.

Workup

  1. customat ambient temperature
  2. stirringAfter stirring for 3.5 hours at the same temperature
  3. customthe mixture was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in a mixture of diethyl ether and 0.5N aqueous sulfuric acid
  5. customThe separated organic layer was dried
  6. customevaporated under reduced pressure
  7. customThe residue was triturated in petroleum ether
  8. customto remove impurities
  9. filtrationby filtration
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-aabc65c077044c1ea6fd055d72473db4
Source dataset
uspto-grants-1985_12
Patent number
US04562179

Reaction notes

Loading…