Abstract
The crucial factor of the reaction of 2,6-di-tert-butylphenol with alkali hydroxides is temperature, depending on which two types of potassium or sodium 2,6-di-tert-butylphenoxides are formed. These types exhibit different catalytic activity in the alkylation of 2,6-di-tert-butylphenol with methyl acrylate. More active forms of 2,6-But 2C6H3OK or 2,6-But 2C6H3ONa are synthesized at temperatures higher than 160 °C and are predominantly the monomers, which dimerize on cooling. The data of 1H NMR, electronic, and IR spectra for the corresponding forms of 2,6-But 2C6H3OK and 2,6-But 2C6H3ONa isolated in the individual state are in agreement with cyclohexadienone structure. In DMSO or DMF, the dimeric forms of 2,6-di-tert-butylphenoxides react with methyl acrylate to form methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate in 64–92% yield.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
US Pat. 3277148 (1966); Chem. Abstrs, 1966, 65, 18535.
US Pat. 3526668 (1970); Chem. Abstrs, 1970, 73, 98589.
Jpn Pat. 161350 (1981); Chem. Abstrs, 1982, 96, 162344.
US Pat. 5264612 (1993); Chem. Abstrs, 1993, 120, 191356.
US Pat. 5177247 (1993); Chem. Abstrs, 1993, 116, 6249.
G. Stillson, J. Am. Chem. Soc., 1946, 68, 722.
A. A. Volod’kin and G. E. Zaikov, Izv. Akad. Nauk, Ser. Khim., 2002, 2031 [Russ. Chem. Bull., Int. Ed., 2002, 51, 2189].
A. A. Volod’kin and G. E. Zaikov, Ros. Khim. Zh., 2000, 44, No. 2, 81 [Mendeleev Chem. J., 2000, 44, No. 2 (Engl. Transl.)].
A. A. Volod’kin, V. I. Paramonov, F. M. Egidis, and L. K. Popov, Khim. prom-st’ [Chemical Industry], 1988, No. 12, 7 (in Russian).
A. A. Volod’kin, Izv. Akad. Nauk, Ser. Khim., 1994, 827 [Russ. Chem. Bull., 1994, 43, 769 (Engl. Transl.)].
A. A. Volod’kin, A. S. Zaitsev, V. L. Rubailo, V. A. Belyakov, and G. E. Zaikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 1829 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 38, 1677 (Engl. Transl.)].
T. F. Titova, A. P. Krysin, V. A. Bulgakov, and V. I. Mamatyuk, Zh. Org. Khim,, 1984, 20, 1899 [J. Org. Chem. USSR, 1984, 20 (Engl. Transl.)].
V. A. Bulgakov, N. N. Gorodetskaya, G. A. Nikiforov, and V. V. Ershov, Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 71 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983, 32 (Engl. Transl.)].
K. Shobatake and K. Nakamoto, J. Inorg. Chim. Acta, 1970, 4, 485.
E. Muller, P. Ziemek, and A. Rieker, Tetrahedron Lett., 1964, No. 4, 207.
E. Yu. Bekhli, D. D. Novikov, and S. G. Entelis, Vysokomolek. Soedin., Ser. A, 1967, 9, 2754 [Polym. Sci., Ser. A, 1967, 9 (Engl. Transl.)].
N. A. Malysheva, A. I. Prokof’ev, N. N. Bubnov, S. P. Solodovnikov, T. I. Prokof’eva, A. A. Volod’kin, and V. V. Ershov, Izv. Akad. Nauk SSSR, Ser. Khim., 1977, 1522 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1977, 26 (Engl. Transl.)].
L. PaQuette and W. Farley, J. Org. Chem., 1967, 32, 2718.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2138–2143, December, 2006.
Rights and permissions
About this article
Cite this article
Volod’kin, A.A., Zaikov, G.E. Potassium and sodium 2,6-di-tert-butylphenoxides and their properties. Russ Chem Bull 55, 2220–2225 (2006). https://doi.org/10.1007/s11172-006-0575-6
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0575-6