反应详情

A mixture of 1,12-dodecanediol (2,2 g, 0.011 mol), sodium hydride (0.91 g. 0.023 mol, 61%) and 25 ml of dry dimethylformamide were stirred under a nitrogen atmosphere at 90°-95° C. for 12 hours. After cooling, 4.0 g (0.23 mol) of 4-nitrophthalonitrile was added to the white salt mixture. The salt dissolved quickly and the mixture was heated at 100°-110° C. for 4 hours. Infrared analysis indicated that a large quantity of 4-nitrophthalonitrile was still present. The temperature was increased to 140°-145° C. and the mixture was stirred at this temperature for 15 hours. The cooled reaction mixture was poured into 200 ml of cold water and the product was extracted into three, 75 ml portions of methylene chloride. The combined extract was washed several times with water, charcoaled, dried over anhydrous sodium sulfate, and concentrated at reduced pressure. Recrystallization of the crude material from ethanol-water yielded 1.7 g (40%) of 1,12-bis(3,4-dicyanophenoxy) dodecane.

1. temperatureAfter cooling
2. dissolutionThe salt dissolved quickly
3. temperaturethe mixture was heated at 100°-110° C. for 4 hours
4. temperatureThe temperature was increased to 140°-145° C.
5. stirringthe mixture was stirred at this temperature for 15 hours
6. customThe cooled reaction mixture
7. extractionthe product was extracted into three, 75 ml portions of methylene chloride
8. extractionThe combined extract
9. washwas washed several times with water
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated at reduced pressure
12. customRecrystallization of the crude material from ethanol-water