Esterification: Methods, Reactions, and Applications (2nd by Junzo Otera, Joji Nishikido

By Junzo Otera, Joji Nishikido

Collecting jointly the common literature within the box, this monograph acts as a reference consultant to this vitally important chemical response. Following an advent, the booklet is going directly to speak about method, earlier than treating man made and business purposes -- the latter being a brand new concentration during this thoroughly revised, up to date and prolonged moment version.
A must-have for natural, usual items and catalytic chemists, in addition to these operating in undefined, of for academics in chemistry.

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Additional info for Esterification: Methods, Reactions, and Applications (2nd Edition)

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GCMS analysis of an aliquot shows complete conversion of starting material into the desired product after 24 h. A solution of hydrogen chloride in dioxane (4 M, 2 mL) is added to the mixture, and after this has been stirred for 1 h the excess solvent is evaporated. The residue is dissolved in ether or dichloromethane and shaken vigorously with magnesium sulfate, and the solvent is evaporated. Flash column chromatography (20% ethyl acetate in hexanes) gives the desired benzyl ester as a pale yellow oil (86 mg, 69%).

Otherwise difficult-to-achieve esterification of benzoic acids with phenols is feasible [200]. Inversion of sterically hindered 17-hydroxy steroids [201] and regioselective esterification of sucrose [202] are feasible. 30 When the alcohol is sterically hindered, the acyloxyphosphonium intermediate in route B plays a key role. The acyloxy-alkoxy interchange is suppressed, and so the acyl carbon of the acyloxyphosphonium species is directly attacked by the alkoxy anion [203, 204]. 31. 31 Despite its various advantages, the Mitsunobu process suffers from a serious problem due to the unavoidable use of large amounts of the reagents, the separation of by-products thus occasionally being tedious and problematic.

The use of fluorous azodicarboxylate derivatives is another means by which the separation problem may be solved (see Part Two). Bistridecafluorooctyl azodicarboxylate is one such reagent, readily recovered from the reaction mixture simply by extraction with FC-72 (perfluorohexanes) [210]. The combined use of fluorous azidocarboxylate and tertiary phosphine provides further elaboration of separation [211]. The activity of the Mitsunobu reagent may be enhanced. Azodicarboxamides in place of esters can activate less reactive acids.

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