47157-01-7Relevant articles and documents
Metal triflate formation of C12-C22phenolic compounds by the simultaneous C-O breaking and C-C coupling of benzyl phenyl ether
Hossain, Md. Anwar,Maihom, Thana,Mills, Kyle,Molley, Ashten,Rahaman, Mohammad Shahinur,Sathitsuksanoh, Noppadon,Tulaphol, Sarttrawut,Yelle, Daniel
supporting information, p. 17390 - 17396 (2021/12/10)
Catalytic pathways to produce high carbon number compounds from benzyl phenyl ether require multiple steps to break the aryl etheric carbon-oxygen bonds; these steps are followed by energy-intensive processes to remove oxygen atoms and/or carbon-carbon coupling. Here, we show an upgrading strategy to transform benzyl phenyl ether into large phenolic (C12-C22) compounds by a one-step C-O breaking and C-C coupling catalyzed by metal triflates under a mild condition (100 °C and 1 bar). Hafnium triflate was the most selective for the desired products. In addition, we measured the effect of solvent polarity on the catalytic performance. Solvents with a polarity index of less than 3.4 promoted the catalytic activity and selectivity to C12-C22 phenolic products. These C12-C22 phenolic compounds have potential applications for phenol-formaldehyde polymers, diesel/jet fuels, and liquid organic hydrogen carriers. This journal is
Cobalt-Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes
Lee, Jeonghyo,Kang, Bora,Kim, Dongwook,Lee, Jia,Chang, Sukbok
supporting information, p. 18406 - 18412 (2021/11/16)
We herein disclose the Cp*Co(III)(LX)-catalyzed amidative alkyl migration using 2,6-disubstituted phenyl azidoformates. Upon the cobalt-nitrenoid insertion toward the substituted ortho carbon, an arenium cationic species bearing a quaternary carbon is generated, and a subsequent alkyl migration process is suggested to occur through an unforeseen alkyl-walking mechanism. A quinolinol ligand of the cobalt catalyst system is proposed to facilitate the final product-releasing rearomatization process by serving as an internal base. This new mechanistic mode enabled both [1,2]- and [1,4]-alkyl rearrangements to allow the structural variation of N-heterocyclic compounds.
Towards ortho-selective electrophilic substitution/addition to phenolates in anhydrous solvents
Lopu?anskaja, Eleana,Kooli, Anni,Paju, Anne,J?rving, Ivar,Lopp, Margus
, (2021/02/16)
Alkyl-substituted Li-phenolates with BnBr in water solution lead to a mixture of o- and p-Bn-substituted phenols together with a substantial amount of phenol Bn ether. In CPME, and especially in toluene with 1–2 equivalents of ether or alcohol additives, ortho-selective alkylation is achieved. In the case of o,o,p-tri- and o,o-di-substituted phenols dearomatization occurs affording o-Bn-substituted alkyl cyclohexadienones with yields up to 92% with an o/p ratio up to 90/1.
METHOD OF MAKING BENZYLATED PHENOLS
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Page/Page column 9-10, (2008/06/13)
A method of making benzylated phenols comprises contacting a phenol and a benzyl alcohol with a basic metal oxide catalyst at a temperature sufficient to maintain each of the phenol and the benzyl alcohol in a vapor phase. The phenol has at least one hydr
The reaction of nitrile oxide-quinone cycloadducts. III. Reinvestigation of the base-induced isomerization of the 1:1 -C=C-adducts of aromatic nitrile oxides with 2,5-and 2,6-dialkyl-substituted p-benzoquinones
Mukawa, Takashi,Inoue, Yukihiko,Shiraishi, Shinsaku
, p. 2549 - 2556 (2007/10/03)
The structure of the product obtained by the base, induced isomerization of the 1,3-dipolar cycloadduct of 2,5-di-t-butyl-p-benzoquinone with 2,6- dichlorobenzonitrile oxide was determined by X-ray analysis. The t-butyl group at the bridgehead position of the 1,3-dipolar cycloadduct migrated to the neighboring carbonyl carbon atom. This base-induced rearrangement took place with a bulky group, i.e., Et, i-Pr, t-Bu, and Bn at the bridgehead position of nitrile oxide-quinone cycloadducts in an alcoholic media. The driving force of this reaction is considered to be due to stabilization by aromatization from isoxazoline derivatives to isoxazole-fused p-quinol derivatives.
ALKYLATION OF PHENOL BY ALCOHOLS IN THE PRESENCE OF ALUMINUM PHENOLATE
Koshchii, V. A.,Kozlikovskii, Ya. B.,Matyusha, A. A.
, p. 1358 - 1361 (2007/10/02)
The reaction of phenol with alcohols in the presence of aluminum phenolate leads to a mixture of 2- and 4-alkylphenols, of which the former predominate in the case of benzyl, tert-butyl, and cyclohexyl alcohols, and the latter in the case of dimethylphenyl- and diphenylmethylcarbinols.Only triphenyl(4-hydroxyphenyl)methane is formed during the alkylation of phenol by triphenylcarbinol.In individual experiments the formation of small amounts of alkyl phenyl ethers and 2,6-dialkylphenols was observed.
ALKYLATION OF ACTIVE HYDROGEN COMPOUNDS WITH ALLYLIC AND BENZYLIC ALCOHOLS UNDER CoCl2 CATALYSIS. A USEFUL SYNTHESIS OF GRIFOLIN
Marquet, J.,Moreno-Manas, M.
, p. 173 - 176 (2007/10/02)
CoCl2 is a useful catalyst for the condensation of allylic and benzylic alcohols with active hydrogen compounds.Under these neutral conditions orcinol and farnesol react to afford the antibiotic grifolin.
