Bulletin of the Chemical Society of Japan p. 416 - 420 (1984)
Update date:2022-09-26
Topics:
Tashiro, Masashi
Itoh, Takashi
Fukata, Gouki
Reaction of 4-halocyclohexadienones such as 4-bromo-(1a), 4-chloro-2,4,6-tri-t-butyl-(1b), 2,4-dichloro-4,6-di-t-butyl-2,5-cyclohexadien-1-one, and 2,4-dichloro-2,6-di-t-butyl-3,5-cyclohexadien-1-one with phenols in the presence of α-picoline was carried out under various conditions.The reaction of 1a and 1b with phenols afforded the corresponding 2-aryloxy-4,6-di-t-butyl phenols together with various by-products.The AlCl3 catalyzed trans-t-butylation of 2-aroxy-4,6-di-t-butyl-phenols, which were obtained by the above reaction, afforded the corresponding 2-hydroxyphenyl aryl ethers.The similar reaction of 4-aroxy-2,4,6-tri-t-butyl-2,5-cyclohexadien-1-ones also afforded the corresponding 4-hydroxyphenyl aryl ethers.
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