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Report | Regular issue | Vol 19, No. 8, 1982, pp.1487-1495
Published online, 1st January, 1970
DOI: 10.3987/R-1982-08-1487
Cyclodienones. 9. Reaction of 4-Halo-2,4,6-tri-tert-butyl-2,5-cyclohexadien-1-ones with Pyrazoles and Preparation of 1-(2-Hydroxyphenyl)- and 1-(4-Hydroxyphenyl)pyrazoles

Gouki Fukata, Takashi Itoh, and Masashi Tashiro

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

Abstract

Reaction of 4-halo-2,4,6-tri-tert-butyl-2,5-cyclohexadien-1-one (1) with pyrazoles (8) afforded 4-(pyrazol-1-yl)-2,4,6-tri-tert-butyl-2,5-cyclohexadien-1-one (9), 1-(4-hydroxy-3,5-di-tert-butylphenyl)- and 1-(2-hydroxy-3,5-di-tert-butylphenyl)pyrazoles (10 and 11) together with by-products. De-tert-butylation of 9,10 and 11 was carried out in boiling 85% H3PO4 to give the corresponding 1-(4-hydroxyphenyl)- and 1-(2-hydroxyphenyl)pyrazoles (17 and 18) in good yields, respectively.