Organic Lab Reactions 109

Organic Lab Reactions 109 - 35% NaOH 35% NaOH -14% KOH 15%...

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104 THE CANNIZZARO REACTION reaction having no serious limitations. When the substituent is a func- tional group the Cannizzaro reaction proceeds normally except in a few special cases, namely, o- and p-hydroxybenzaldehyde and p-di- methylaminobenzaldehyde. It is probable that o- and p-amino- and alkylamino-benzaldehydes would also fail to undergo normal dismuta- tion, but examples have not been described. It has been reported 61 that jw-dimethylaminobenzaldehyde is unaffected by strong aqueous alkali. TABLE III 2XCjH4-CHO +OH " -> XC 6 H 4 CH 3 OH +XC 6 H 4 COO - x= 4-CHs 4-*-C 8 H 7 2-OCH» * 2-OCHs 3-OCHa 4-OCH3 3-OCH3 3-OH 3-C1 3--Br 2-1 4-1 2-NO2 3-NO2 3-NO2 4-NO2 4-NO2 Alkali * Ale. KOH Cone. ale. KOH 25% ale. KOH , Cone. KOH 25% ale. KOH 25% ale. KOH Cone. ale. KOH 50% KOH 50% KOH 50% KOH 50% ale. KOH 50% ale. KOH
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Unformatted text preview: 35% NaOH 35% NaOH -14% KOH 15% NaOH 35% NaOH Yield of X CH 4 CH2OH 90% 92-97% 89% -90% 81% 91% 90% 96% X-C 6 H 4 COOH 76% 94% 90% 88% 90% 87.5% 84% 91% 90% 90% Reference 62 63 64 65 64 64 66 67 68 68 68 68 68 68 69,70 71 68 * Aqueous unless otherwise stated el Cocker, Hams, and Loach, J. Chem. Soc., 1938, 751. 62 Cannizzaro, Ann., 124, 255 (1862). M Kraut, Ann., 92, 66 (1854). M Spath, Monatsh., 34, 1996 (1913). 'Stoermer, Ber., 44, 1850 (1911). 66 Pschorr, Ann., 391, 43 (1912). Lock, Ber., 62, 1177 (1929). ! Lock, Ber., 63, 855 (1930). M Becker, Ber., 15, 2090 (1882). 70 Lock, Ber., 66, 1527 (1933). 71 Busier, Ber., 16, 275 (1883)....
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