Nitric Acid → 6-(4-Nitrophenyl)hexanoic acid

Participants

Reaction Conditions

Reaction Steps

6-Phenylhexanoic acid (30 g) was added dropwise over 6.5 hours to 125 ml of 90% nitric acid with cooling to -30° to -20° C. When the addition was complete, the mixture was allowed to warm to -10° C. for 30 minutes and it was then poured into ice water. The resulting mixture was extracted with diethyl ether and the ether extract was washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then evaporated to leave a crude yellow solid which was subjected to high pressure liquid chromatography using ethyl acetate/hexane/glacial acetic acid as the eluent. This chromatography removed dinitrated material and gave a yellow slush which was recrystallized from a mixture of toluene and hexane to give 6-(4-nitrophenyl)hexanoic acid.

Provenance & Evidence