Sulfuric Acid → 4-(2H-Tetrazol-2-yl)phenol

Participants

Reaction Conditions

Reaction Steps

The crude 4-(2H-tetrazol-2-yl)aniline (60 mg, 0372 mmol) was suspended in water (2 mL) and sulfuric acid (0.2 mL) before cooling to 0° C. An aqueous solution of sodium nitrite (26 mg, 0.565 mmol) in water (2 mL) was added. The mixture was stirred at 0° C. for 30 min. Additional water (1 mL) and sulfuric acid (0.37 mL) was added and the mixture heated at 120° C. for 1 hour. The reaction was then cooled and extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, concentrated and purified by preparative TLC eluting with 30% ethyl acetate/hexanes to give the desired phenol product as yellow solid. LRMS calc: 162.1; obs: 163.2 (M+1).

Provenance & Evidence