Kinetic study of the acid-catalyzed rearrangement of 4-acetyl-3, 3-dimethyl-5-hydroxy-2-morpholino-2, 3-dihydrobenzo [b] furan

…, JG Santos, JC Valcarcel, JA Valderrama

Index: Castro, Christian G.; Santos, Jose G.; Valcarcel, Juan C.; Valderrama, Jaime A. Journal of Organic Chemistry, 1983 , vol. 48, # 18 p. 3026 - 3029

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Citation Number: 17

Abstract

A kinetic study of the acid-catalyzed rearrangement of the title compound (6) to form 5, 8- dihydroxy-4, 4-dimethyl-l (4H)-naphthalenone (4) in dioxane-water, ethanol-water, and ethanol-dioxane is reported. In water mixtures the presence of 4-acetyl-2, 5-dihydroxy-3, 3- dimethyl-2, 3-dihydrobenzo [blfuran (7) is detected, and it slowly leads to the rearrangement product 4. The rate constant of the transformation 6-4 is more than 1Wfold faster than 7-4, ...