反応 #1134576

反応方程式

hydrochloric acid

1-docosanol

Sodium hydride

1,12-dibromododecane

→

12-docosyloxy-dodecyl bromide

収率 78.0%

溶媒

toluene

hexane

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   その他in a water bath to quench
3. 3
   その他the reaction
4. 4
   抽出The mixture was extracted with chloroform (100 ml)
5. 5
   洗浄washed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml)
6. 6
   乾燥The organic layer was dried over sodium sulfate
7. 7
   その他the solvent of the filtrate was evaporated
8. 8
   その他The residue was isolated
9. 9
   その他purified by silica gel column chromatography
10. 10
    その他precipitated with methanol (70 ml)

実験手順

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%).

出典