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Communication | Regular issue | Vol 12, No. 12, 1979, pp.1551-1554
Published online, 1st January, 1970
DOI: 10.3987/R-1979-12-1551
2,5-Cyclohexadienones. 1. A Novel Formation of 1-(3,5-Di-t-butyl-1-hydroxyphenyl)pyridinium Bromide

Masashi Tashiro* and Gouki Fukata

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


The reaction of 4-bromo-2,4,6-tri-t-butyl-2,5-cyclohexadien-1-one (1) with pyridine (3) afforded 1-(3,5-di-t-butyl-2-hydroxyphenyl)pyridinium bromide (4) in 20% yield, which gave easily 2,4-di-t-butyl-6-(1-pyridinio)phenolate (10) by the treatment with strong base such as DBU. It was also found in this reaction that addition of ethylene glycol increased the yield of 4 from 20% to 45%. The reduction of 4 and 10 with sodium borohydride afforded same product, 2,4-di-t-butyl-6-(1,2,3,6-tetrahydro-1-pyridyl)phenol (11). A tentative mechanistic interpretation for the formation of 4 is also proposed.