반응 #1134576

반응 방정식

hydrochloric acid

1-docosanol

Sodium hydride

1,12-dibromododecane

→

12-docosyloxy-dodecyl bromide

수율 78.0%

용매

toluene

hexane

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   기타in a water bath to quench
3. 3
   기타the reaction
4. 4
   추출The mixture was extracted with chloroform (100 ml)
5. 5
   세척washed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml)
6. 6
   건조The organic layer was dried over sodium sulfate
7. 7
   기타the solvent of the filtrate was evaporated
8. 8
   기타The residue was isolated
9. 9
   기타purified by silica gel column chromatography
10. 10
    기타precipitated with methanol (70 ml)

실험 절차

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%).

출처