Study of the exchange reaction of benzoic and 2-chlorobenzoic anhydrides in chloroform. Effects of pyridine 1-oxide and benzoate salts

Add time:08/27/2019    Source:sciencedirect.com

Benzoic anhydride ((PhCO)2O) and 2-chlorobenzoic anhydride ((2-ClC6H4CO)2O) undergo slow exchange reaction in CHCl3 to produce mixed benzoic 2-chlorobenzoic anhydride (2-ClC6H4COOCOPh). The rate of conversion changes abnormally with the concentration ratio of [(PhCO)2O]/[(2-ClC6H4CO)2O]. The reaction is catalyzed by pyridine 1-oxide (PNO). When (2-ClC6H4CO)2O is the limiting reactant, the presence of benzoate salt promotes the reaction substantially with the order of effectiveness being PhCOOLi, PhCOONBu4>PhCOONa>PhCOOH. This exchange reaction does not follow simple second-order or pseudo-first-order kinetics. However, under pseudo-order reaction condition and in the presence of PNO or benzoate salt, the reaction follows pseudo-first-order kinetics. The mechanism of the reaction is more complicated than expected. Mechanistic rationalization of experimental results is presented.

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