Bruice, Thomas C. published the artcileA search for carboxyl-group catalysis in ketal hydrolysis, Recommanded Product: 2,2,4-Trimethyl-1,3-dioxolane, the publication is Journal of the American Chemical Society (1967), 89(14), 3568-76, database is CAplus.
The pH-rate profiles for the hydrolysis of 19 1,3-dioxanes and 1,3-dioxolanes, seven of which were carboxyl substituted, were determined The rates of hydrolysis were not sensitive to the concentration of formate and acetate buffers at constant pH showing the compounds were not susceptible to intermol. general acid catalyzed hydrolysis. The log of the pseudo-first-order rate constants (kobsd) for the hydrolysis of all dioxolanes and dioxanes not substituted by carboxyl groups when plotted vs. pH provided linear plots of slope ∼-1.0 indicating the mechanism of hydrolysis is specific acid catalysis. For the carboxyl-substituted dioxolanes and dioxanes, the pH-log kobsd profiles are characterized by the superimposition of a plateau rate upon the specific acid catalyzed region, followed in the low acid region by a descending leg of approx. slope of -1.0. The plateau and second descending leg have kinetically equivalent interpretations as participation by the undissociated carboxyl group in the hydrolysis or the specific acid catalyzed hydrolysis of the carboxylate anion form of the ketals. The latter mechanism is correct on the basis that the log krate values for the calculated constants for specific acid catalyzed hydrolysis of the undissociated ketals (K-CO2H) and dissociated ketals (K-CO2-) exhibit no pos. deviations from Hammett plots (σ*) constructed from the rate constants for specific acid catalysis of the hydrolysis of ketals not containing carboxyl groups. Literature reports of the participation of neighboring carboxyl groups in the hydrolysis of acetals are discussed. 32 references.
Journal of the American Chemical Society published new progress about 1193-11-9. 1193-11-9 belongs to dioxole, auxiliary class Dioxolanes, name is 2,2,4-Trimethyl-1,3-dioxolane, and the molecular formula is C6H12O2, Recommanded Product: 2,2,4-Trimethyl-1,3-dioxolane.
Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem