Mechanistic interpretation of the simultaneous hydrolysis and methanolysis of chloromethyl chloroacetate in weakly acidic aqueous methanol solutions of varying solvent composition
Abstract
The simultaneous hydrolysis and methanolysis of chloromethyl chloroacetate in aqueous methanol at xw from 1.00 to 0.50 in 0.01 to 0.06 mol dm–3 perchloric acid solutions have been studied. The methanolysis of the ester in anhydrous and in highly alcohol-rich methanolic hydrogen chloride solutions up to 0.2 mol dm–3 acid has also been studied. Under the reaction conditions, the neutral BAC3 reactions are accompanied by the acid-catalysed reactions. The kinetic data are in accord with the conclusion that the acid-catalysed reactions take place simultaneously by the AAC2 and A–BAC3 mechanisms, at least at xw >0.5. The extent to which the AAC2 mechanism operates with increased methanol content and in methanol the reaction takes place solely by the AAC2 mechanism.