Abstract
The catalytic properties of alumoxane compounds in the alkylation of 4-methoxyphenol with styrene were studied. Structures and yields of aikylation products depend on the amount of catalyst, the phenol: olefin ratio, and the reaction time. Phenoxyalumoxanes are effectiveortho-directing catalysts with respect to the hydroxy group. Under optimum conditions, 2-(α-methylbenzyl)-4-methoxyphenol and 2,5-di-(α-methylbenzyl)-4-methoxyphenol were obtained in 94 % and 84–86 % yields, respectively.
References
J. Silar, J. Kahovec, and J. Pospisil,Chem. Prum., 1970,20, 521.
Ja. B. Kozlikovsky, V. A. Koschii, and S. A. Butov,Zh. Org. Chem., 1986,22, 606 [J. Org. Chem. USSR, 1986,22 (Engl. Transl.)].
Ja. B. Kozlikovsky, V. A. Koschii, S. A. Butov, and T. F. Ovsiiuk,Zh. Org. Chem., 1988,24, 827 [J. Org. Chem. USSR, 1988,24 (Engl. Transl.)].
N. M. Emanuel, inPuti sinteza i izyskaniya protivoopukholevykh preparatov [Search for New Antitumor Drugs and Their Syntheses], Medgiz, Moscow, 1962 (in Russian).
M. V. Kurashev, V. N. Perchenko, R. Sh. Abubakirov, F. Kh. Inoyatov, and V. L. Khodzhayeva,Neftekhimia [Petroleum Chemistry], 1991,31, 809 (in Russian.)
J. Lukasiak, L. A. May, J. Y. Strauss, and R. Piekos,Roczn. Chem., 1970,44, L1675.
M. V. Kurashev, and N. N. Korneev,Neftekhimia [Petroleum Chemistry], 1988,28, 176 (in Russian.)
M. V. Kurashev, A. I. Yanovsky, and Yu. T. Struchkov,Izv. Akad. Nauk SSSR, 1988, 1098 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 961 (Engl. Transl.)].
V. N. Perchenko, R. Sh. Abubakirov, M. V. Kurashev, O. B. Semenov, I. M. Khrapova and N. A. Plate.,Dokl. Akad. Nauk SSSR, 1992,326, 276 [Dokl. Chem., 1992, 326 (Engl. Transl.)].
G. V. Lisichkin, and A. Ya. Juffa, in:Geterogennye metallokompleksnye katalizatory [Metal Complexes as Heterogeneous Catalysts], Khimia, Moscow, 1981 (in Russian.)
Ja. B. Kozlikovsky, B. V. Chernyaev, A. L. Litvin, and A. V. Kofinova,Zh. Org. Chem., 1986,22, 1469 [Russ. J. Org. Chem., 1986,22 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 992–994, May, 1993.
Rights and permissions
About this article
Cite this article
Inoyatov, F.K., Abubakirov, R.S., Mikaya, A.I. et al. Alkylation of 4-methoxyphenol with styrene in the presence of alumoxane compounds. Russ Chem Bull 42, 955–958 (1993). https://doi.org/10.1007/BF00698972
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00698972