Acetic Acid → 3-(1H-tetrazol-1-yl)phenol

Participants

Reaction Steps

To a 200 ml round bottom flask equipped with a magnetic stir bar containing a solution of 3-aminophenol (5 g, 45.8 mmol, 1.0 eq) in triethyl orthoformate (24.4 ml, 146.5 mmol, 3.2 eq) was added sodium azide (3.73 g, 57.3 mmol, 1.25 eq) and acetic acid (41.95 ml, 732.8 mmol, 16.0 eq). The mixture was stirred for 10 min at room temperature and then heated at 80° C. for 1.5 h. After heating, the mixture was bronze and homogeneous. The mixture was cooled to room temperature. Water (30 mL) and 6 N HCl (17 mL) was added. A 25% aqueous solution of NaNO2 (6 mL) was slowly added while the reaction mixture was cooled in an ice bath. A white solid, 3-tetrazol-1-yl-phenol 29 (5.3 g, 72% yield) was obtained upon filtration and washing with water. LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 163.0 (M+H)+1 1H-NMR, Varian 400 MHz (MeOH-d4) δ 9.71 (s, 1H), 7.41 (t, 1H), 7.28 (d, 2H), 6.96 (d, 1H) ppm.

Provenance & Evidence