Journal of the American Chemical Society

Formation and hydrolysis of lactones of phenolic acids

M Caswell, GL Schmir

Index: Caswell, Michael; Schmir, Gaston L. Journal of the American Chemical Society, 1980 , vol. 102, # 14 p. 4815 - 4821

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Citation Number: 49

Abstract

Abstract: The lactonization of 2'-hydroxybiphenyl-2-carboxylic acid to 3, 4-benzocoumarin has been studied in aqueous solution, 30 OC, in the range of pH 0-6.5. As with simpler coumarinic acids, the rate-determining step changes from the breakdown of tetrahedral intermediates in the neutral or weakly acidic pH range to formation of intermediates below pH 2. In contrast, the lactonization of methyl-substituted dihydrocoumarinic acids shows ...