1-Chloro-2-nitrobenzene → Sulfolane

Participants

Reaction Conditions

Reaction Steps

1,300 parts of o-chloronitrobenzene, 960 parts of potassium fluoride and 82.5 parts of 18-crown-6 in 1,300 parts of tetramethylenesulfone are stirred under nitrogen for 30 hours at 180° C. The solution is cooled to 110° C. and filtered, the solid residue is rinsed with 500 parts of methylene chloride and the filtrates are combined and distilled. 932 parts (80% of theory) of o-fluoronitrobenzene of boiling point 55°-57° C./1.2 mm Hg and 1,290 parts (99.2% of theory) of tetramethylenesulfone of boiling point 105°-110° C. are obtained. About 70% of the crown ether can be recovered from the distillation residue by repeated extraction by shaking with water.

Provenance & Evidence