Abstract
A derivative of aspirin, (1′-ethoxy)ethyl 2-acetoxybenzoate, was synthesized and its hydrolysis was studied in aqueous solution. The rate of hydrolysis was followed spectrophotometrically and found to be: (a) first order with respect to the compound, (b) independent of pH, (c) very sensitive to solvent polarity, and (d) an isotope effect (k/D2o/k/D2o) near unity. Based on these results, the hydrolysis of the derivative appears to proceed by a classical SN1-type mechanism.
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