4-Aminobenzoic Acid → 4-{[(benzyloxy)carbonyl]amino}benzoic acid

Participants

Reaction Steps

Aqueous NaOH (2N, 1.93 g, 48.3 mmol) was added to a solution of 4-aminobenzoic acid (3.0 g, 21.90 mmol) in H2O at 0° C. A clear solution appeared within 5 min. Then, benzyl carbonochloridate (4.45 g, 26.28 mmol) was added dropwise to the mixture and it was heated to room temperature and stirred for 2 h. The reaction mixture was diluted with water and separated with ether. The aqueous layer was cooled to 0° C. temperature and acidified with 6M HCl. The solid was collected by filtration, washed with water and dried. The crude solid was recrystallized from ethyl acetate-hexane to furnish 4-(benzyloxycarbonylamino)benzoic acid 10 (5.0 g, 84%) as a white solid.

Provenance & Evidence