The intramolecular Cannizzaro reaction of phthalaldehyde

Abstract
Phthalaldehyde undergoes an intramolecular Cannizzaro reaction in aqueous base to produce the o-hydroxymethylbenzoate ion. The kinetics of the reaction have been measured over a range of sodium hydroxide concentration at 40 °C. The reaction is considerably slower than that of the analogous reaction of phenylglyoxal since it proceeds exclusively via the cyclic hydrate dianion which must undergo a very unfavorable ring opening before internal hydride transfer can occur.

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