반응 #94455

반응 방정식

diisobutylaluminum hydride

water

1,4-bis(2-methyl-2-cyanopropyl)tetramethylbenzene

water

→

1,4-bis(2,2-dimethyl-3-aminopropyl)tetramethylbenzene

용매

toluene

methanol

toluene

methanol

반응 조건

후처리

1. 1
   기타In a 1-liter flask, equipped
2. 2
   온도The mixture was refluxed for 22 hrs
3. 3
   온도After the mixture had been cooled in an ice-water bath
4. 4
   workup.STIRRINGwith stirring
5. 5
   workup.STIRRINGThe mixture was then stirred at room temperature for several hours
6. 6
   workup.WAITto stand at room temperature for 3 days
7. 7
   여과The mixture was filtered under nitrogen
8. 8
   세척the solid was washed thoroughly with toluene on the filter
9. 9
   workup.DISTILLATIONthe combined filtrate and rinsings were distilled on the water pump
10. 10
    기타A solid residue resulted which
11. 11
    기타after further drying in a vacuum oven at room temperature

실험 절차

In a 1-liter flask, equipped as described in Example 9(a), was put 6.17 g of 1,4-bis(2-methyl-2-cyanopropyl)tetramethylbenzene and 200 ml of reagent grade toluene which had been passed through acid alumina under nitrogen directly into the reaction vessel. With stirring at room temperature, 71.3 ml of a 24.1% solution of diisobutylaluminum hydride in toluene was added in 25 min. The mixture was refluxed for 22 hrs and allowed to stand at room temperature for 3 days. After the mixture had been cooled in an ice-water bath, a solution of 4 ml of water in 20 ml of methanol was added dropwise with stirring. This was followed by the dropwise addition of a solution of 20 ml of water in 40 ml of methanol. The mixture was then stirred at room temperature for several hours and allowed to stand at room temperature for 3 days. 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. A solid residue resulted which, after further drying in a vacuum oven at room temperature, weighed 5.21 g and melted at 97°-99°. Sublimation of this material at 125°-145°/0.50 mm gave 1,4-bis(2,2-dimethyl-3-aminopropyl)tetramethylbenzene as a colorless crystalline solid melting at 97.5°-98.5°.

출처