Benzoic Acid → 1-(Benzoyloxy)-1H-1,2,3-benzotriazole

Participants

Reaction Steps

Benzoic acid (2.44 g) is dissolved in a solution of triethylamine (2.80 ml) in dichloromethane (20 ml) under ice-cooling. To the solution is added 1-methanesulfonyloxy-1,2,3-benzotriazole (4.26 g) and the mixture is stirred at room temperature for 3 hours. The reaction mixture is washed with water, a saturated aqueous sodium hydrogen carbonate and water in order and dried to give crystals of 1-benzoyloxy-1,2,3-benzotriazole (5.0 g). The product is dissolved in dichloromethane (20 ml) and thereto are added triethylamine (2.80 ml) and methanol (4.8 ml) and the mixture is stirred at room temperature for 1 hour. The reaction mixture is washed with water, an aqueous sodium hydrogen carbonate and water in order, dried and then the solvent is distilled off to give methyl benzoate (2.39 g). Infrared spectrum: 1728 cm-1.

Provenance & Evidence