Inverse Phase Transfer Catalysis. Kinetics and Mechanism of the Pyridine 1-Oxide-Catalyzed Substitution Reaction of Benzoyl Chloride and Benzoate Ion in a Two-Phase Water/Dichloromethane Medium

Article abstract of DOI:10.1021/jo00033a018

The two-phase reaction of benzoyl chloride (PhCOCl) and benzoate ion with pyridine 1-oxide (PNO) as the phase transfer catalyst yields both the substitution product (benzoic anhydride) and the hydrolysis product (benzoic acid).A high yield (<*>95 percent) of benzoic anhydride can be obtained if a polar organic solvent like dichloromethane is used.Under appropriate conditions, this reaction follows the rate law -d_org/dt = (k_h + k_{c iaq})_org.The effects of agitation rate, organic solvent, ionic strength, temperature, and the concentrations of reactants and catalyst on the reaction rate were investigated.A mechanism to rationalize the kinetic results is also given.