Nitric Acid → 1-(2,2-Dichlorocyclopropyl)-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

Nitric acid (25 g.) was added during three hours to a mixture of (2,2-dichlorocyclopropyl)benzene (45 g.), water (13 g.), acetic acid (40 g.) and concentrated sulfuric acid (177 g.) with cooling (to 3-5° C.). The resulting mixture was quenched in a mixture of ice (400 g.) and chloroform (200 g.). The layers were separated and the aqueous layer was washed with chloroform (100 g.). The chloroform layers were combined and washed with aqueous sodium carbonate (5%, 300 ml.). The sodium carbonate layer was backwashed with chloroform (75 g.). The combined chloroform extracts were dried, fitered and concentrated, affording p-(2,2-dichlorocyclopropyl)nitrobenzene mixed with the ortho isomer (57 g.).

Provenance & Evidence