Reaktion #660211

Reaktionsgleichung

hydrochloric acid

1-docosanol

Sodium hydride

1,12-dibromododecane

→

12-docosyloxy-dodecyl bromide

Ausbeute 78.0%

Lösungsmittel

toluene

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Sonstigein a water bath to quench
3. 3
   Sonstigethe reaction
4. 4
   ExtraktionThe mixture was extracted with chloroform (100 ml)
5. 5
   Waschenwashed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml)
6. 6
   TrocknenThe organic layer was dried over sodium sulfate
7. 7
   Sonstigethe solvent of the filtrate was evaporated
8. 8
   SonstigeThe residue was isolated
9. 9
   Sonstigepurified by silica gel column chromatography
10. 10
    Sonstigeprecipitated with methanol (70 ml)

Vorschrift

Sodium hydride (60%, 0.98 g, 24.5 mmol) washed with hexane was suspended in toluene (16 ml), 1-docosanol (4.00 g, 12.2 mmol) was added, 1,12-dibromododecane (8.04 g, 24.5 mmol) was added, and the mixture was stirred at 85° C. for 2 days. The reaction mixture was cooled to room temperature, 1N hydrochloric acid (30 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (100 ml), and washed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml), and once with 20% aqueous sodium chloride solution (30 ml). The organic layer was dried over sodium sulfate, and the solvent of the filtrate was evaporated. The residue was isolated and purified by silica gel column chromatography and precipitated with methanol (70 ml) to give 12-docosyloxy-dodecyl bromide (yield 78%).

Quelle