Journal of the American Chemical Society

Reactions of Vanillin and its Derived Compounds. XVIII. 1 Preparation and Reactions of Lignin Model Substances Related to 5-Carboxyvanillic Acid2, 3

IA Pearl, DL Beyer

Index: Pearl; Beyer Journal of the American Chemical Society, 1952 , vol. 74, p. 3188

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Citation Number: 8

Abstract

5-Allylvanillin was isomerized by low temperature caustic fusion io yield 5-propenylvanillin. Ethyl vanillate and ethyl orthovanillate were converted to ethyl 5-allylvanillate and ethyl 5- allylorthovanillate, respectively, and these were treated directly with fused caustic to yield 5- propenylvanillic acid and 5-propenylorthovanillic acid. Oxidation of the propenyl compounds with nitrobenzene and alkali at 160-165" gave the corresponding formyl derivatives as the ...