18626-98-7Relevant articles and documents
Mechanistic Study of a Re-Catalyzed Monoalkylation of Phenols
Lehnherr, Dan,Wang, Xiao,Peng, Feng,Reibarkh, Mikhail,Weisel, Mark,Maloney, Kevin M.
, p. 103 - 118 (2018/11/06)
A mechanistic study of a rhenium catalyzed monoalkylation of phenols is described. Reaction kinetics reveals a zero-order dependence on both alkene and phenol and a half order dependence on catalyst. Isotopic labeling studies, competition experiments, kinetic isotope effects, and Hammett analysis together afford experimental data consistent with a reversible C-H activation step and an irreversible hydrometalation process. The turnover-limiting step is identified as catalyst deaggregation. NMR studies of binary mixtures of catalyst and a single substrate (alkene or phenol) as well as those of reaction mixtures identify potential intermediates and off-cycle species. Despite the numerous Re complexes formed in these mixtures, the overall reaction is both high yielding and highly selective for monoalkylation of phenols.
Alkylation of phenol with olefins in the presence of lignosulfonic acids
Pisanenko,Smirnov-Zamkov
, p. 1655 - 1657 (2007/10/03)
Alkylation of phenol with cyclohexene, 1-octene, dicyclopentadiene, 1,3-cyclopentadiene, and butylene polymer distillate at 100-140°C was studied. The process was performed in the presence of lignosulfonic acids obtained from industrial calcium lignosulfonates.
ALKYLATION OF PHENOL BY CHLOROALKANES IN THE PRESENCE OF ALUMINUM PHENOLATE
Kozlikovskii, Ya. B.,Koshchii, V. A.,Butov, S. A.
, p. 128 - 131 (2007/10/02)
The alkylation of phenol by benzyl chloride, 1-chloroadamantane, and tert-butyl chloride in the presence of aluminum phenolate leads to a mixture of the corresponding 2- and 4-alkylphenols and 2,6-dialkylphenols, in which the 2-alkylphenol usually predominates.During the alkylation of phenol by 2-chlorooctane 2- and 4-(3-octyl)phenols and 2- and 3-octyl phenyl ethers are formed in addition to 2- and 4-(2-octyl)phenols.