110920-08-6Relevant 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 (1997)
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.
ORTHO-ALKYLATION OF PHENOL WITH 2-HEXENE AND 2-OCTENE IN THE PRESENCE OF ALUMINUM PHENOLATE
Kozlikovskii, Ya. B.,Koshchii, V. A.,Ovsiyuk, T. F.
, p. 49 - 54 (2007/10/02)
The alkylation of phenol with 2-hexene and 2-octene in the presence of aluminum phenolate leads to a mixture of corresponding 3- and 2-alkyl phenyl ethers 2-(3-alkyl)-, 2-(2-alkyl)-, and 4-(2-alkyl)phenols, 2-(2-alkyl)-6-(3-alkyl)phenols, and 2,6-di(2-alkyl)phenols.The overall yield of the products from ortho-alkylation amounts to 90-95percent, and the ortho-para ratio is larger than 14:1.
