Nitric Acid → 1-(4-Nitrophenyl)-1,2-cyclopropanedicarboxylic acid
Reaction equation
[C:1]1([C:7]2([C:13]([OH:15])=[O:14])[CH2:9][CH:8]2[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22]>>[N+:21]([C:4]1[CH:3]=[CH:2][C:1]([C:7]2([C:13]([OH:15])=[O:14])[CH2:9][CH:8]2[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:23])=[O:22]Participants
4
Procedure
To a stirred slurry of 20.6 g. of 1-phenylcyclopropane-1,2-dicarboxylic acid (J. Med. Chem. 24:481) in 25 ml. of concentrated sulfuric acid at 0° C. is added 15 ml. of concentrated nitric acid over 30 minutes. The resultant solution is stirred at ambient temperature for 30 minutes and then poured onto ice. The crystalline product is recrystallized from hexane-ethyl acetate to give 1-(p-nitrophenyl)-cyclopropane-1,2-dicarboxylic acid as colorless crystals.