反应详情

温度

100 °C

A mixture of 1,12-dodecanediol (2.2 g, 0.011 mol), anhydrous potassium carbonate (4.1 g, 0.031 mol), 35 ml of dimethylformamide and 5 ml of benzene was heated at reflux under a nitrogen atmosphere for 12 hours. A small quantity of water was collected in a Dean-Stark trap. The benzene was removed by distillation. To the cooled reaction medium was added 4.0 g (0.023 mol) of 4-nitrophthalonitrile, which resulted in an immediate color change to a deep blue. After 10 minutes at room temperature, the reaction medium had turned to a yellowish-orange and remained this color throughout the entire reaction. The mixture was stirred and heated at 100° C. for 16 hours under a nitrogen atmosphere. The cooled reaction mixture was poured into 200 ml of cold dilute hydrochloric acid and extracted with three 75 ml portions of chloroform. The combined extract was washed with water, dried over anhydrous sodium sulfate, charcoaled and concentrated at reduced pressure. Recrystallization of the crude produced from ethanol-water yielded 3.1 g (70%) of 1,12-bis(3,4-dicyanophenoxy) dodecane.

1. temperaturewas heated
2. temperatureat reflux under a nitrogen atmosphere for 12 hours
3. customA small quantity of water was collected in a Dean-Stark trap
4. customThe benzene was removed by distillation
5. customTo the cooled reaction medium
6. customresulted in an immediate color change to a deep blue
7. customthroughout the entire reaction
8. customThe cooled reaction mixture
9. extractionextracted with three 75 ml portions of chloroform
10. extractionThe combined extract
11. washwas washed with water
12. dry with materialdried over anhydrous sodium sulfate
13. concentrationconcentrated at reduced pressure
14. customRecrystallization of the crude
15. customproduced from ethanol-water