527-35-5Relevant articles and documents
Pentamethylphenyl (Ph*) and Related Derivatives as Useful Acyl Protecting Groups for Organic Synthesis: A Preliminary Study
Cheong, Choon Boon,Frost, James R.,Donohoe, Timothy J.
, p. 1828 - 1832 (2020/10/06)
A study of acyl protecting groups derived from the Ph? motif is reported. While initial studies indicated that a variety of functional groups were not compatible with the Br 2-mediated cleavage conditions required to release the Ph? group, strategies involving the use of different reagents or a modification of Ph? itself (Ph*OH) were investigated to solve this problem.
Phenolic Oxidation Using H2O2 via in Situ Generated para-Quinone Methides for the Preparation of para-Spiroepoxydienones
McLaughlin, Michael F.,Massolo, Elisabetta,Cope, Thomas A.,Johnson, Jeffrey S.
supporting information, p. 6504 - 6507 (2019/09/04)
Phenols are attractive starting materials for the preparation of highly substituted cyclohexane rings via dearomative processes. Herein we report an efficient preparation of dearomatized 1-oxaspiro[2.5]octa-4,7-dien-6-ones (para-spiroepoxydienones) via the nucleophilic epoxidation of in situ generated para-quinone methides from 4-(hydroxymethyl)phenols using aqueous H2O2. The developed protocol bypasses the need for stoichiometric bismuth reagents or diazomethane, which are frequently deployed for p-spiroepoxydienone preparation. The p-spiroepoxydienones are further elaborated in numerous downstream complexity-building transformations.
Experimental Investigation on Upgrading of Lignin-Derived Bio-Oils: Kinetic Analysis of Anisole Conversion on Sulfided CoMo/Al2O3 Catalyst
Rahimpour, Hamid Reza,Saidi, Majid,Rostami, Parisa,Gates, Bruce C.,Rahimpour, Mohammad Reza
, p. 702 - 713 (2016/09/28)
Kinetics of the hydroprocessing of anisole, a compound representative of lignin-derived bio-oils, catalyzed by a commercial sulfided CoMo/Al2O3, was determined at 8–20 bar pressure and 573–673 K with a once-through flow reactor. The catalyst was sulfided in an atmosphere of H2 + H2S prior to the measurement of its performance. Selectivity-conversion data were used as a basis for determining an approximate, partially quantified reaction network showing that hydrodeoxygenation (HDO), hydrogenolysis, and alkylation reactions take place simultaneously. The data indicate that these reactions can be stopped at the point where HDO is virtually completed and hydrogenation reactions (and thus H2 consumption) are minimized. Phenol was the major product of the reactions, with direct deoxygenation of anisole to give benzene being kinetically almost insignificant under our conditions. We infer that the scission of the Cmethyl–O bond is more facile than the scission of the Caromatic–O bond, so that the HDO of anisole likely proceeds substantially through the reactive intermediate phenol to give transalkylation products such as 2-methylphenol. The data determine rates of formation of the major primary products. The data show that if oxygen removal is the main processing goal, higher temperatures and lower pressures are favored.
