Hydrochloric Acid → 1,12-Bis(3,4-dicyanophenoxy) dodecane

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence