Abstract
The chloromethylation of benzo-1,4-dioxane in acetic acid in presence of SnCl4, SbCl3, ZnCl2, and SbCl5 catalysts was investigated. The activation energy of the process was found to be 19.6 kcal/mole. The reaction is zero order in chloride ion and first order in the Hammett acidity function. In excess HCl the reaction is described by a second-order equation. The relative activities of the methyl chlorides in the chloromethylation of benzo-1,4-dioxane were determined.
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Literature cited
R. M. Elderfield, (editor), Heterocyclic Compounds, Vol. 6, Wiley (1957).
V. Daukshas and É. Udrenaite, Khim. Geterotsikl. Soedin., No. 9, 1155 (1975).
Z. Bidlo and F. Vonaseh, Prumysl. Potravin., 9, 589 (1958).
I. Drabek, Chem. Zvesti, 10, 357 (1956).
F. Dallacker and J. Bloemen. Monatsh. Chem., 92, 640 (1961).
K. Hejno and Z. Arnold, Chem. Listy, 47, 601 (1953).
I. R. Greigy, British Patent No. 566732; Chem. Abstr., 41, 1250 (1947).
V. Daukshas and P. Kadzyauskas, Nauchn. Tr. Vyssh. Uchebn. Lit. SSR, Ser. Khim., 3, 51 (1963).
J. Ogata and M. Okano, J. Am. Chem. Soc., 75, 5423 (1956).
A. I. Gel'bshtein, G. G. Shcheglova, and M. I. Temkin, Dokl. Akad. Nauk SSSR, 107, 108 (1956).
N. M. Émanuél' and D. G. Knorre, Course in Chemical Kinetics [in Russian], Moscow (1962), p. 50.
K. Laidler, Kinetics of Organic Reactions [Russian translation], Mir, Moscow (1966), p. 341.
A. Sh. Shatenshtein, Isotope Exchange and Hydrogen Substitution in Organic Compounds [in Russian], Izd. Akad. Nauk SSSR, Moscow (1960), p. 63.
C. Kelley and P. McCusker, J. Am. Chem. Soc., 65, 1307 (1943).
J. Lewis, J. R. Millee, R. L. Richards, and A. Thompson, J. Am. Chem. Soc., 11, 5850 (1965).
A. E. Agronomov and Yu. S. Shabarov, Laboratory Work in a Practical Organic Course [in Russian], Khimiya, Moscow (1974), p. 63.
J. Walker, Formaldehyde, Reinhold (1953).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 459–462, April, 1981.
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Lyushin, M.M., Bakus, P.Y. & Nagiev, A.I. Kinetics of chloromethylation of benzo-1,4-dioxane. Chem Heterocycl Compd 17, 324–328 (1981). https://doi.org/10.1007/BF00503326
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DOI: https://doi.org/10.1007/BF00503326