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Organic Lab Reactions 114

Organic Lab Reactions 114 - a variety of structural...

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THE CROSSED CAtfNIZZARO REACTION 109 dismutation products could be isolated. a-Pyrrolaldehyde appears to be stable to alkali. 88 ' The Crossed Cannizzaro Reaction Examples of this reaction have long been known, and several have been discussed above (pp. 99-102). Applications of the method to aldehydes of the aromatic series have been reported more recently. Nenitzescu and Gavat 89 observed that equimolal mixtures 'of benzalde- hyde or anisaldehyde with formaldehyde led to the formation of both possible acids and alcohols, and that if formaldehyde was present in large excess the aromatic alcohol, and little of the corresponding acid, was formed. The procedure may therefore be looked upon as a method for reducing aromatic aldehydes. Davidson and Bogert 90 have worked out experimental conditions for carrying out the reduction of aldehydes by this means to give 85-90% yields of the alcohols. Studies of the crossed Cannizzaro reaction have not embraced so wide
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Unformatted text preview: a variety of structural modifications as the examples discussed above in connection with the normal dismutation. There is reason to believe, TABLE VI RCHO + HjCO OH-RCH 2 OH Aldehyde Veratraldehyde Piperonaldehyde Anisaldehyde Opianic acid Phthaldehydic acid Anisaldehyde Furfuraldehyde m-Nitrobenzaldehyde p-Isopropylbenzaldehyde p-Phenylbenz aldehyde Yield of Alcohol 85-90% 85-90% 85-90% 70-90% 70-90% 70-90% 70-90% — 42% — Reference 90 90 89,90 91 91 91 91 89 92 93 88 Fischer, Beller, and Stern, Ber., 61, 1074 (1928). M Nenitzescu and Gavat, Bui. Soc. Chim. Rom&nia, 16A, 42 (1934) [C. A., 30, 5572 (1936)]. 80 Davidson and Bogert, J. Am. Chem. Soc., 67, 905 (1935). 91 Rodinor and Fedorova, J. Gen. Chem. U.S.S.R., 7, 947 (1937) [C. A., 31, 5338 (1937)] 92 Cooke, Gillespie, and Macbeth, J. Chem. Soc, 1938, 1825. 98 Koelsch and Geissman, unpublished observation....
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