Document Type

Research

Abstract

Benzaldehyde¹ and its alkyl, alkoxy and halogen substitution products are readily oxidized to the corresponding acids. Contact with air often brings about the change.² Biicking,³ and Fittig and Remsen⁴ found that p-hydroxybenzaldehyde and protocatechuic aldehyde, respectively, are not readily oxidized by potassium permanganate solution. Tiemann⁵ could not oxidize vanillin, the 3-methyl ether of protocatechuic aldehyde, into vanillin acid by the usual methods, and Brady and Dunn⁶ failed to oxidize 5- bromovanillin with acetic acid solution of chromic acid and also by alkaline solution of potassium permanganate. The behavior of many vanillin substitution products⁷ toward the last-named reagent is now being studied. If the hydroxyl group in position 4 is exposed almost all the starting material is recovered. When the alkyl derivatives are used the corresponding acids are obtained. Results thus far indicate that the weight of the alkyl group may determine the yield of product. When a heavy alkyl is present the yield is low. 1 Wohler and Liebig, Ann., 3,250 (1832). 2 Bornemann, Ber., 17, 1466 (1884). 3 Bucking, Ber., 9,529 (1876). 4 Fittig and Remsen, Ann., 159, 150 (1871). 5 Tiemann, Ber., 9, 415 (1876). 6 Brady and Dunn, J. Chem. Soc., 107, 1859 (1915). 7 Raiford and Wells, J. Am. Chem. Soc., 57, 2500 (1935).

Publication Date

1940

Journal Title

Proceedings of the Iowa Academy of Science

Volume

Issue

First Page

264

Last Page

265

Copyright

Language

File Format

application/pdf

Recommended Citation

Perry, R. P. and Raiford, L. Charles (1940) "Behavior of Some P-Hydroxybenzaldehyde Derivatives toward Oxidizing Agents," Proceedings of the Iowa Academy of Science, 47(1), 264-265.
Available at: https://scholarworks.uni.edu/pias/vol47/iss1/54

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Behavior of Some P-Hydroxybenzaldehyde Derivatives toward Oxidizing Agents

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