5454-22-8Relevant academic research and scientific papers
Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives
Hayashi, Hiroyuki,Yasukochi, Shotaro,Sakamoto, Tatsuhiro,Hatano, Manabu,Ishihara, Kazuaki
, p. 5197 - 5212 (2021/04/12)
Insight into the mechanism of a safe, simple, and inexpensive phosphoric acid (H3PO4)-catalyzed acylation of alcohols with acid anhydrides is described. The corresponding in situ-generated diacylated mixed anhydrides, unlike traditionally proposed monoacylated mixed anhydrides, are proposed as the active species. In particular, the diacylated mixed anhydrides act as efficient catalytic acyl transfer reagents rather than as Br?nsted acid catalysts simply activating acid anhydrides. Remarkably, highly efficient phosphoric acid (1-3 mol %)-catalyzed acylation of alcohols with acid anhydrides was achieved and a 23 g scale synthesis of an ester was demonstrated. Also, phosphoric acid catalyst was effective for synthetically useful esterification from carboxylic acids, alcohols, and acid anhydride. Moreover, with regard to recent developments in chiral 1,1′-bi-2-naphthol (BINOL)-derived phosphoric acid diester catalysts toward asymmetric kinetic resolution of alcohols by acylation, some phosphate diesters were examined. As a result, a 31P NMR study and a kinetics study strongly supported not only the acid-base cooperative mechanism as previously proposed by other researchers but also the mixed anhydride mechanism as presently proposed by us.
Perfume compositions
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, (2008/06/13)
The perfume compositions of this invention include one or more of 3-methylnonan-3-ol, 3-methyl-1-nonen-3-ol, 3-methylnonan-1-ol, 3-methyl-2-nonen-1-ol and the monocarboxylic acid esters of these alcohols. The perfume compositions also contain a perfume component, the odoriferous properties of which are enhanced and modified by said alcohols or esters of the alcohols without chemical reaction.
