Oxidation of 4-Acyloxy Derivatives of Cinnamic Acid

Authors

Victor S. Webster, State University of IowaFollow
L. Chas. Raiford, State University of IowaFollow

Document Type

Research

Abstract

It is known that benzaldehyde (17) and its alkyl, alkoxy and halogen substitution products are easily oxidized to the corresponding acids. In many cases contact with air brings about the change (4). The presence of hydroxyl as a substituent often makes the aldehyde less reactive toward oxidizing agents. For example, Bücking (3) and Fitting and Remsen (5) reported that p-hydroxybenzaldehyde and protocatechuic aldehyde, respectively, are not readily oxidized by potassium permanganate solution, but require fusion with caustic potash to give the related acids. Tiemann (13) found that when vanillin, the 3-methyl ether of protocateuchuic aldehyde, is treated with oxidizing agents hardly any change takes place or else complete decomposition occurs, depending on conditions, while Brady and Dunn (2) failed to oxidize 5-bromovanillin with acetic acid solution of chromic acid and also by alkaline solution of potassium permanganate.

Publication Date

1940

Journal Title

Proceedings of the Iowa Academy of Science

Volume

47

Issue

1

First Page

249

Last Page

255

Copyright

©1940 Iowa Academy of Science, Inc.

Language

en

File Format

application/pdf

Recommended Citation

Webster, Victor S. and Raiford, L. Chas. (1940) "Oxidation of 4-Acyloxy Derivatives of Cinnamic Acid," Proceedings of the Iowa Academy of Science, 47(1), 249-255.
Available at: https://scholarworks.uni.edu/pias/vol47/iss1/47