反应详情

In a 2-liter flask, equipped as described in Example 1(b), was put 10.90 g of 3,3'-bis(2-methyl-2-cyanopropyl)biphenyl and 500 ml of reagent grade toluene which had been passed through acid alumina under nitrogen directly into the reaction vessel. With stirring at room temperature, 118 ml of a 25% solution of diisobutylaluminum hydride in toluene was added in 25 minutes. The mixture was refluxed for 18 hrs, and then allowed to stand at room temperature for 1 day. After the mixture had been cooled in an ice-water bath, a solution of 7 ml of water in 35 ml of methanol was added dropwise with stirring. This was followed by the dropwise addition of a solution of 33 ml of water in 66 ml of methanol. The ice-water bath was removed, and the mixture was stirred for 1 hour. The mixture was filtered under nitrogen, the solid was washed thoroughly with toluene on the filter, and the combined filtrate and rinsings were distilled on the water pump. The cloudy viscous residue weighed 10.8 g after it was evacuated for several hours with the oil pump at room temperature. Distillation of this material through a small Vigreux still gave 5.94 g of 3,3'-bis(2,2-dimethyl-3-aminopropyl)biphenyl as a clear, colorless, viscous liquid boiling at 159° to 168°/0.2-0.5 mm.

1. customIn a 2-liter flask, equipped
2. temperatureThe mixture was refluxed for 18 hrs
3. temperatureAfter the mixture had been cooled in an ice-water bath
4. stirringwith stirring
5. customThe ice-water bath was removed
6. stirringthe mixture was stirred for 1 hour
7. filtrationThe mixture was filtered under nitrogen
8. washthe solid was washed thoroughly with toluene on the filter
9. distillationthe combined filtrate and rinsings were distilled on the water pump
10. customwas evacuated for several hours with the oil pump at room temperature
11. distillationDistillation of this material through a small Vigreux still gave 5.94 g of 3,3'-bis(2,2-dimethyl-3-aminopropyl)biphenyl as a clear, colorless, viscous liquid boiling at 159° to 168°/0.2-0.5 mm