Phenyl benzoate transesterification

The rates and mechanisms of hydrolysis and transesterification of phenyl benzoate in aqueous ethanolic KOH solution were determined by non-linear least-squares regression.4 Kinetic studies of the transesterification of a series of 4-nitrophenyl 3- and 4-substituted benzoates by 4-chlorophenol in DMF in the presence of potassium carbonate at various temperatures were reported.5... 

Transesterification of 4-nitrophenyl benzoate (6 Y = 4-N02) with a series of Z-substituted phenoxides (7 Z = 4-Me, H, 3-Cl, 4-MeCO, 4-CN) and of a series of eight Y-phenyl benzoates (6) by 4-chlorophenoxide (7 Z = 4-Cl) (Scheme 3) in H2O/DMSO (dimethylsulfoxide) (4 1) at 298 K both exhibited linear Brpnsted plots with slopes, respectively, of /Sjjuc = 0.72 and /Sjg = -0.62, the magnitude of each value indicating a concerted mechanism for both reactions. ... 

The carbonate linkage can react with the ester linkage in a transesterification reaction. This reaction is illustrated by the reaction of diphenyl carbonate with butylene dibenzoate to form phenyl benzoate. 

Figure 5.191 uses the sodium benzoate-induced melt crystallization of bisphenol A-polycarbonate to illustrate its catalyzed decomposition. There are kinetic and product specific indications that rearrangements of phenyl salicylates are forming o-phenoxybenzoates. The phenyl salicylates are created by sodium salicylates that form from carboxylate ions of sodium phenolate. Pyrolysis/mass spectroscopic investigations showed the ultimate formation of cyclical trimmers, dimers, and/or tetramers of bisphenol A-polycarbonate caused by intermolecular transesterifications and/or homolytic reactions [673]. 

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