21566-82-5Relevant academic research and scientific papers
Acidity effect in the regiochemical control of the alkylation of phenol with alkenes
Sartori, Giovanni,Bigi, Franca,Maggi, Raimondo,Arienti, Attilio
, p. 257 - 260 (2007/10/03)
Treatment of 1:1 mixtures of phenol and linear alkenes in the presence of an acidic promoter in CHCl3 at room temperature results in ortho-regioselective monoalkylation producing sec-alkylphenols in 48-60% yield. In similar reactions, branched alkenes lead exclusively to the corresponding para-tert-alkylphenols in 80-85% yield. Addition of increasing amounts of potassium phenolate to the reacting system reduces the protic acidity and promotes ortho-regioselective tert-alkylation. These results are tentatively explained in terms of competition of 'H-bond-template' and 'charge-controlled' mechanisms.
Alkylation of Phenol by 1-Dodecene and 1-Decanol. A Literature Correction
Campbell, Curt B.,Onopchenko, Anatoli,Santilli, Donald S.
, p. 3665 - 3669 (2007/10/02)
A recent literature report that 1-dodecene reacts with phenol in the presence of sulfated zirconium oxide (superacid), or 1-dodecanol with phenol in the presence of H-Mordenite (zeolite), to afford mostly para-substituted alkylphenols has been shown to be incorrect.The product with zirconium is a mixture of ortho/para isomers (ca. 50-65/50-35), and not the exclusive para isomer as reported.The major product in the case of zeolite catalysis is the o-alkylphenol, with a high degree of end attachment, and not the predominantly claimed para isomers.The selectivity obtained with H-Mordenite during alkylation of phenol differs from the a lkylation of alkylbenzenes and anisole, and is best explained on the basis of a surface catalysis phenomenon.
REACTION OF PHENOL WITH 1-DODECENE IN THE PRESENCE OF ALUMINUM PHENOLATE
Kozlikovskii, Ya. B.,Koshchii, V. A.,Butov, S. A.,Vykhrestyuk, N. I.
, p. 1183 - 1186 (2007/10/02)
The reaction of phenol with 1-dodecene in the presence of aluminum phenolate leads to a mixture of products of the phenol and ether types.The products from orthoalkylation of the phenol predominate, and 2-(3-dodecyl)- and 2-(4-dodecyl)phenols are formed in addition to 2-(2-dodecyl)phenol.
