Abstract
Abstract A new route to the syntheses of 4-methyldihydrocoumarins has been developed by means of the aluminum chloride-catalyzed reaction of phenols with allyl cyanide. The reaction of excess phenol with allyl cyanide in the presence of 2 equivalents of anhydrous aluminum chloride and an excess of hydrogen chloride yielded β-(p-hydroxyphenyl)-butyronitrile in a 16% yield. In contrast, the corresponding 4-methyldihydrocoumarins were obtained, together with β-arylbutyronitriles, from o- and m-cresols. p-Cresol gave rise to 4,6-dimethyldihydrocoumarin as the sole product in a 8% yield. In diisopropyl ether, resorcinol underwent a similar reaction with allyl cyanide and afforded 4-methyldihydroumbelliferone in a 50% yield.
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