2,6-Dihydroxybenzoic Acid → 2,6-Diacetoxybenzoic acid

Participants

Reaction Steps

A solution of 2,6-dihydroxybenzoic acid (4.72 g, 30 mmol) in Ac2O (16 g, 14.2 mL) containing 5 drops of conc. H2SO4 was heated with stirring at 80° for 2 hr until tlc analysis indicated the reaction was complete. The solution was poured onto ice/H2O and extracted 3× with EtOAc. The combined organic phases were washed 4× with H2O and once with brine prior to drying over Na2SO4. After removal of the volatiles using a rotary evaporator, 5.8 g of 2,6-diacetoxybenzoic acid was obtained as a white solid which was used without further purification.

Provenance & Evidence