4-Trifluoromethylbenzyl chloride: preparation kinetics and mechanism of its change into bis [4-trifluoromethylbenzyl] ether in alkaline dioxane-water media

The expected alpha-proton abstraction step from the title compound by alkali in dioxane-water media, due to the electron-withdrawing 4-trifluoromethyl group, does not take place instead an S [N]2 reaction followed by an etherification step occurs. This consecutive reaction was studied kinetically in different dioxane-water media at various temperatures