Reacción #1134576

Ecuación de reacción

hydrochloric acid

1-docosanol

Sodium hydride

1,12-dibromododecane

→

12-docosyloxy-dodecyl bromide

Rendimiento 78.0%

Disolventes

toluene

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   Otroin a water bath to quench
3. 3
   Otrothe reaction
4. 4
   ExtracciónThe mixture was extracted with chloroform (100 ml)
5. 5
   Lavadowashed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml)
6. 6
   SecadoThe organic layer was dried over sodium sulfate
7. 7
   Otrothe solvent of the filtrate was evaporated
8. 8
   OtroThe residue was isolated
9. 9
   Otropurified by silica gel column chromatography
10. 10
    Otroprecipitated with methanol (70 ml)

Procedimiento

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%).

Fuente