Download e-book for iPad: Oxidation of primary alcohols to carboxylic acids : a guide by Gabriel Tojo

By Gabriel Tojo

As the second one quantity in a finished encyclopedia of natural reactions, this paintings offers an elaborated description of the experimental tools used for the oxidation of alcohols to acids. It provides vital info on attainable interferences from preserving teams and sensible teams, in addition to on strength side-reactions. This publication is a needs to for somebody excited about the education of natural compounds.

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Extra resources for Oxidation of primary alcohols to carboxylic acids : a guide to current common practice

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When the reaction is performed on a multigram scale, a long mixing period is necessary to avoid overheating. The oxidation must be carried out under some kind of temperature control. The reaction is most often performed at 0 C, although temperatures as low as −25 C are possible. The control of reaction temperature sometimes consists simply of adjusting the addition rate so as to prevent overheating above room temperature. 0 equivalent of CrO3 . g Sometimes, the quantity of oxidant is adjusted using a titrating protocol in which a “normal” addition is employed and Jones reagent is added to the solution of alcohol in acetone until persistence of Jones reagent color is observed.

Soc. 1988, 110, 5547. Chem. 1987, 52, 5048. 26 a) Marshall, J. ; Gung, W. ; Tetrahedron Lett. 1988, 29, 3899. Chem. 2004, 12, 3203. ; Panek, J. Soc. 2002, 124, 11368. 27 a) Martin, S. ; Dappen, M. ; Murphy, C. ; Colapret, J. Chem. 1989, 54, 2209. ; Tetrahedron: Asymmetry 2004, 15, 1331. ; Baker, T. Lett. 2000, 2, 2967. ; Tetrahedron: Asymmetry 2000, 11, 2403. 30 a) Avery, M. ; Karle, J. ; Bonk, J. ; Goins, D. Chem. 1996, 39, 1885. b) Charette, A. Soc. 1995, 117, 12721. 1. Introduction In the 1940s, Heyns et al.

49 Chapter 2 23 The very acid-sensitive THP ether is hydrolyzed under the acidic conditions of Jones oxidation, resulting in an alcohol that is transformed in situ into a carboxylic acid that can be isolated as lactone. 49 Regarding acetals protecting 1,2- and 1,3-diols, it has been reported that benzylidene, 50 isopropylidene, 51 cyclohexylidene, 19 and methylene 52 acetals resist the action of Jones reagent while an alcohol is oxidized to a carboxylic acid. Depending on substrate and exact reaction conditions, dioxolanes protecting aldehydes and ketones can both be hydrolyzed 53 or remain unchanged 54 during the oxidation of primary alcohols with Jones reagent.

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