Nitric Acid → 4-(4-Methoxycarbonylphenyl)-2-nitrophenol

Participants

Reaction Steps

Concentrated nitric acid (1.8 ml) was carefully added to a cooled suspension (5-10° C.) of phenol 27 (2.0 mg, 8.8 mmol) in 60 ml of glacial acetic acid. The reaction mixture was stirred for one hour and was then allowed to warm to room temperature and stirred for an additional 30 minutes. Water was added (50 ml) and the reaction mixture was cooled, filtered, and washed with water to yield a yellow powder. The crude product was purified via flash chromatography through a small pad of silica gel with elutions of 80/20 and 50/50 (Hex/EtOAc), respectively. Evaporation of the solvent yielded 2.23 g (93%) of a bright yellow solid.

Provenance & Evidence