2,6-Dihydroxybenzoic Acid → 2,6-Diacetoxybenzoic acid
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([OH:6])=[O:5]>CC(OC(C)=O)=O.OS(O)(=O)=O>[C:2]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:7](=[O:11])[CH3:8])[C:3]=1[C:4]([OH:6])=[O:5])(=[O:1])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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.