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The nuclear alkylation of phenol by t-butyl chloride is inhibited by dioxane, the decrease in reaction rate being proportional t o the concentration of dioxane. The inhibition can be quantitatively accommodated by assuming that a hydrogenbonded complex of 2: 1 pheno1:dioxane is formed, and that phenol so bound cannot participate in the alkylation reaction. The same explanation fits the data for tetrahydropyran if a 1 : 1 complex is assumed. The availability of the phenolic hy. droxyl, presumably for solvating the halogen of the alkyl halide, thus appears significant in the alkylation reaction.

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