The hydrolysis of 2,2,2-trifluoroethyl hydrogen 3,6-dimethylphthalate in acid solution is found to proceed with neighbouring carboxylate anion participation via the anhydride intermediate. The hydrolysis follows the equation: rate =k[ionised ester], and kobs=k/(1 +[H+]/Ka). The 3,6-dimethyl substitution results in a 150-fold increase in hydrolysis rate.
M. D. Hawkins, J. Chem. Soc., Perkin Trans. 2, 1975, 285 DOI: 10.1039/P29750000285
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