By Gabriel Tojo
As the second one quantity in a finished encyclopedia of natural reactions, this paintings offers an elaborated description of the experimental equipment used for the oxidation of alcohols to acids. It provides vital facts on attainable interferences from conserving teams and useful teams, in addition to on power side-reactions. This ebook is a needs to for someone all in favour of the practise of natural compounds.
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Because the moment quantity in a complete encyclopedia of natural reactions, this paintings offers an elaborated description of the experimental equipment used for the oxidation of alcohols to acids. It offers vital information on attainable interferences from preserving teams and practical teams, in addition to on strength side-reactions.
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Additional info for Oxidation of primary alcohols to carboxylic acids : a guide to current common practice
Castilho, M. ; ARKIVOC 2002, VIII, 112. g) Avery, M. ; Karle, J. ; Tetrahedron Lett. 1995, 36, 3965. h) Avery, M. ; Karle, J. ; Bonk, J. ; Goins, D. Chem. 1996, 39, 1885. 24 Cornforth, R. ; Cornforth, J. ; Tetrahedron 1962, 18, 1351. 25 a) Newman, M. Soc. 1960, 82, 2498. b) Mathur, H. ; Bhattacharyya, S. Soc. 1963, 3505. Chem. 2002, 67, 7995. Chem. 2002, 67, 4475. ; Fernández, M. in Basic Reactions in Organic Synthesis. Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice, G.
In this oxidation of a primary alcohol in the presence of a secondary one, it is important not to increase the temperature to maintain good selectivity. 28a Due to the mildness of Heyns oxidation, it is often possible to selectively oxidize certain primary alcohols in molecules possessing more than one alcohol of this kind. 40 The less hindered primary alcohol is selectively oxidized in 80% yield in a molecule containing two primary and two secondary alcohols. 40b 52 General Procedure for Heyns Oxidation of Primary Alcohols Application Heyns oxidation is quite demanding from the experimental point of view; therefore, it must not be recommended for the routine oxidation of primary alcohols to carboxylic acids.
9 A 51% yield of aldehyde is isolated from the oxidation of an alcohol with Jones reagent. The following factors favor an incomplete oxidation of the alcohol: (1) short reaction time, (2) an intermediate aldehyde possessing steric hindrance that disfavors formation of hydrate, and (3) the presence of electron-donating methoxy groups on the benzene ring preventing the buildup of a high concentration of aldehyde hydrate. 71b Sometimes, dimeric esters are obtained from the oxidation of primary alcohols with Jones reagent (see page 15).