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

Participants

Reaction Steps

To a solution of 4-(methylthio)phenol(5.0 g) in methylene chloride (100 mls) was added 30% nitric acid absorbed on silica (9.29 g) and the mixture stirred at room temperature for 3 hrs. The mixture was filtered and washed with methylene chloride. The solvent was evaporated and the residue was purified by flash chromatography eluting with ethyl acetate and hexane (15:85 v/v) to give 2-nitro-4-(methylthio)phenol as an orange solid (2.22 g); NMR (200 MHz, CDCl3): 2.50(3H,s), 7.10(1H,d,J=8 Hz), 7.51(1H,dd,J=8 Hz), 7.95(1H,d,J=3 Hz).

Provenance & Evidence