Conclusions
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1.
The phenoxyl radicals that are formed in the oxidation of the methyl ester ofβ-(3, 5-di-tert-butyl-4-hydroxyphenyl)propionic acid are capable of dimerization, entering into cross recombination, and disproportionation to give the phenol and methylenequinone.
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2.
α-Methylcarboxymethyl-2,6-di-tert-butylmethylenequinone isomerizes spontaneously to the methyl ester ofβ-(3,5-di-tert-butyl-4-hydroxyphenyl)cinnamic acid.
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3.
The stableα-methylcarboxy-2,6-di-tert-butylmethylenequinone was obtained.
Literature cited
V. V. Ershov, A. A. Volod'kin, and G. D. Ostapets-Sveshnikova, Izv. Akad. Nauk SSSR, Ser. Khim., 928 (1966).
L. V. Samsonova, L. Taimr, and J. Pospisil, Angew. Makromol. Chem.,65, 197 (1977).
E. Muller, R. Mayer, H. Spanagel, and K. Scheffler, Ann. Chem.,645, 53 (1961).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2797–2800, December, 1978.
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Kudinova, L.I., Volod'kin, A.A. & Ershov, V.V. Oxidation of methyl ester of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid. Russ Chem Bull 27, 2497–2499 (1978). https://doi.org/10.1007/BF00941107
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DOI: https://doi.org/10.1007/BF00941107