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Unexpected Intermediate 1-Phenyl-2-(4-Pyridyl)Ethanol Isolated From Benzaldehyde and 4-Picoline Condensation Reaction

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The unexpected intermediate 1-phenyl-2-(4-pyridyl)ethanol or 4-[2-(1-hydroxy-1-phenyl)ethyl]pyridine was isolated from the condensation reaction of 4-methylpyridine with benzaldehyde to form the model compound 4-styrylpyridine in the absence of a condensing agent. Spectroscopic data (NMR, IR and UV-VIS) gave evidence that the isolated compound is actually the alcohol just before the dehydration which yields the double bond of the 4-styrylpyridine and the structure was confirmed by single-crystal x-ray analysis.. The isolation method from the reaction mixture was difficult at first, but now a 10 % yield has been obtained, not only in powder form but as crystals good enough for R-X structural analysis.

Affiliations: 1: Centro de Quimica, Instituto de Ciencias, Universidad Autonoma de Puebla, P.O. Box 1613, 72000, Puebla, Puebla, MÉXICO


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