Analysis of the base‐catalyzed phenol–epichlorohydrin condensation

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Abstract
The amount of abnormal addition of phenoxide to epichlorohydrin and phenyl glycidyl ether was determined as a function of reaction conditions. The isomer distribution resulting from attack at either position of these unsymmetrical epoxides was quantitatively measured by vapor phase chromatography of the resulting product mixtures. While both epoxides reacted predominantly in the expected normal fashion, small quantities of abnormal addition products were found whose concentrations were temperature‐dependent. The analytical method also permitted a study of the effect of temperature on side reactions involving hydrolytic solvents.