Reactions of 3-(1-Hydroxyalkyl) phthalides with Acids: Synthesis of (Z)-3-Alkylidenephthalides and 3-Alkyl-8-hydroxyisocoumarins

RS Mali, KN Babu

Index: Mali, Raghao S.; Babu, Kantipudi N. Journal of Organic Chemistry, 1998 , vol. 63, # 8 p. 2488 - 2492

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Citation Number: 67

Abstract

A new acid-catalyzed method for the synthesis of (Z)-3-butylidenephthalides 5 and a novel and general route to 3-alkyl-8-hydroxy/methoxyisocoumarins 6-8 from phthalides 9 is described. The hydroxyphthalides 4 and 10 were obtained by condensation of the phthalide anion with butyraldehyde and acetaldehyde. Reaction of hydroxyphthalides 4 with a mixture of orthophosphoric acid and formic acid gave the (Z)-3-butylidenephthalides 5, while the ...