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Paper | Regular issue | Vol 38, No. 9, 1994, pp.2099-2114
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6829
On the Reaction of Substituted Phenols and 3-Methylbut-2-enoic Acid. A Comparative Study

Péter Sebok, József Jeko, Tibor Tímár,* and Joseph Cs. Jaszberenyi

*Department of Research, Alkaloida Chemical Co. Ltd., H-4440 Tiszavasvári, POB 1, Hungary

Abstract

A systematic and comparative study of the reaction of a series of substituted phenols and 3-methylbut-2-enoic acid in zinc chloride/phosphorus oxychloride and aluminum chloride/phosphorus oxychloride reveals that the formation of phenolic esters and 2,2-dimethyl-4-chromanones is strongly influenced by the substituents, their position on the aromatic ring of the starting phenols. Based on our study, a mixed Friedel-Crafts and Fries rearrangement mechanism is in operation in these reactions.