Highly Selective Vapor and Liquid Phase Transfer Hydrogenation of Diaryl and Polycyclic Ketones with Secondary Alcohols in the Presence of Magnesium Oxide as Catalyst

MgO has been shown to catalyze an almost quantitative hydrogen transfer from 2-octanol as the hydrogen donor to benzophenone to form benzhydrol, a useful intermediate product in the pharmaceutical industry. The hydrogen transfer from a series of alcohols to the carbonyl group of benzophenone, its te...

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Bibliographic Details
Published in:Catalysts 2021-05, Vol.11 (5), p.574
Main Authors: Gliński, Marek, Markowska, Anna, Wrońska, Laura, Jerzak, Anna, Tarkowska, Magdalena
Format: Article
Language:English
Subjects:
2-octanol
Alcohol
benzophenones
Carbonyl groups
Carbonyls
Catalysts
Chemical reactions
Hydrogen
Hydrogenation
Ketones
Liquid phases
Magnesium
Magnesium oxide
Octanol
selective reduction
Superconductors (materials)
transfer hydrogenation
Vapor phases
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Summary:MgO has been shown to catalyze an almost quantitative hydrogen transfer from 2-octanol as the hydrogen donor to benzophenone to form benzhydrol, a useful intermediate product in the pharmaceutical industry. The hydrogen transfer from a series of alcohols to the carbonyl group of benzophenone, its ten derivatives, four polycyclic ketones, and 2-naphthyl phenyl ketone was carried out in liquid (LP) or vapor phase (VP). The dependence of reactivity on the structure of the hydrogen donor, reaction temperature, donor-acceptor ratio, amount of catalyst, and the type and position of substituents has been established. For both reaction modes, optimal conditions for selective synthesis of the alcohols were determined and side reactions were investigated. The results indicate that the reactivity of the ketone is suppressed by the presence of a methyl substituent in the ortho position to a much greater extent in LP mode. A scale-up was demonstrated in the liquid phase mode.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal11050574