Summary
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1.
The alkenylation of p-cresol with phenacyl alcohol in the presence of zinc chloride on aluminum oxide goes in the direction of the formation of 1-phenyl-3-(3-methyl-6-hydroxphenyl)propene-1 in 80% of theoretical yield.
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2.
The alkenylation of p-cresol with phenacyl alcohol proceeds with a larger yield than the allylation of p-cresol, which is explained by the greater stability of the carbo cations of allyl structure formed in the reaction process.
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Literature cited
N. I. Shuikin, E. A. Viktorova, and I. E. Pokrovskaya, Izv. AN SSSR, Otd. khim. n., 1961, 1094.
N. I. Shuikin, E. A. Viktorova, I. E. Pokrovskaya, and T. G. Malysheva, Izv. AN SSSR, Otd. khim. n., 1961, 1660.
Collection, Organic Reactions,6, 432 [Russian translation] (Foreign Literature Publishin House, Moscow).
F. Kremers, F. Roth, and E. Tietze, Liebigs Ann. Chem.,442, 210 (1925).
T. Kenzo, J. Chem. Soc. Japan,80, No. 6, 678 (1959).
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Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12 p. 2216–2217, December, 1964