EFFECT OF HYDROXYL GROUP SUBSTITUENTS ON PYRAN RING ON HYDROLYSIS RATE OF BENZOATES - 2-TETRAHYDROPYRANYL BENZOATE

The hydrolysis of 2‐tetrahydropyranyl benzoate was followed spectrophotometrically at 240 nm and was first order with respect to the compound, independent of pH, and very sensitive to solvent polarity and had an isotope effect (k D 2O/k H 2O) near unity. The pH‐independent hydrolysis rate was about 1 × 106 times faster than that of the corresponding glucosyl benzoate. The results suggest that the presence of hydroxyl groups on the pyran ring has tremendous effect on the hydrolysis rate of these compounds. Copyright © 1979 Wiley‐Liss, Inc., A Wiley Company