Sulfuric Acid → Cyclododecanone

Participants

Reaction Conditions

Reaction Steps

Cyclododecane (3.32 g; 19.8 mmol), N-hydroxyphthalimide (0.8 mmol), and acetic acid (4 ml) were placed in a flask, t-butyl nitrite (6 mmol) was added to the mixture in six installments of 1 mmol each once every 30 minutes with stirring at 70° C. in an atmosphere of argon gas for a total of 3.5 hours. The resulting mixture was further treated with sulfuric acid having a concentration of 98% by weight (200 mg) with stirring at 70° C. for 15 minutes. The reaction mixture was then neutralized with sodium hydroxide and was analyzed to find that cyclododecanone oxime, nitrocyclododecane, and cyclododecanone were formed in yields of 52%, 3%, and 6%, respectively.

Provenance & Evidence