66142-79-8Relevant articles and documents
Selective catalytic carbanionic ethylation of methylphenols: Influence of catalyst and substitution pattern
Steele, Barry R.,Villalonga-Barber, Carolina,Micha-Screttas, Maria,Screttas, Constantinos G.
, p. 2093 - 2097 (2007/10/03)
Addition of ethylene to the carbanions formed by the metallation of the lithium salts of di- and trimethylphenols by the strongly basic system, n-BuLi-LiK(OCH2CH2NMe2)2 provides a useful synthetic route to a range of alkylphenols. The ease of alkylation of the methyl groups decreases in the order ortho>meta>para while the inclusion of Mg(OCH2CH2OEt)2 in the catalyst restricts alkylation to the methyl groups ortho to the hydroxy group. Dialkylation occurs only at the ortho-methyl groups and only if the adjacent meta-position is unsubstituted. The potential of these products for the synthesis of sterically hindered ligands is outlined.