Of alcohols to carboxylic acids

For other examples of alcohol to carboxylic acid oxidations in Ch. 1 cf. 2.3.6. 

Table 2. Oxidation of alcohols to carboxylic acids at the nickel hydroxide electrode Influence of the temperature on the yield...

Potassium nitrosodisulfonate, 258 other methods Bis(tributyltin) oxide, 41 /-Butyl hydroperoxide-Dichlorotris-(triphenylphosphine)rutheni-um(II), 54 Dibutyltin oxide, 95 Hydrogen hexachloroplatinate(IV)-Copper(II) chloride, 145 4-Methoxy-2,2,6,6-tetramethy 1-1 -oxopiperidinium chloride, 183 of alcohols to carboxylic acids Cetyltrimethylammonium permanganate, 69... 

Immobilized TEMPO has been used for the one-pot oxidation of alcohols to carboxylic acids as well.26 For this purpose TEMPO resin 1 was combined with two ion-exchange resins loaded with chlorite anions and hydrogen phosphate in the presence of catalytic amounts of potassium bromide and sodium hypochlorite in solution. The reaction required work-up for the removal of salts, but tolerated several protecting schemes and afforded pure products in good to excellent yields. The reaction is initiated by catalytic TEMPO oxidation of alcohols to aldehydes driven by dissolved hypochlorite followed by oxidation to the carboxylic acids effected by chlorite. 

Immobilized TEMPO radical has also been used for one-pot oxidation of alcohols to carboxylic acids [14]. For this purpose TEMPO-resin 1 was combined with two... 

Platinum(II), for example, K2PtClt, in an aqueous medium in the presence of 02, oxidizes ethane selectively to ethanol and ethylene glycol, whereas metallic Pt is required for the further oxidation of alcohols to carboxylic acids. Platinum metal also catalyzes the oxidation of alkenes to 1,2-diols. The presence of CO prevents further oxidation of the alcohol products.155... 

Other electrosyntheses produce salts of organic acids (e.g., NiOOH oxidations of alcohols to carboxylic acid salts) or—in the case of the electroreduction of aromatic nitro compounds—salts of anilines. To recover the pure organic products, the addition of acids or bases is needed and after separation of organic and salt phases further purification steps are necessary. 

Oxidation of alcohols to carboxylic acids (or ketones) with nickel peroxide (see 1st edition). 

D. Forster and T.W. Dekleva (1986) Journal of Chemical Education, vol. 63, p. 204 - Catalysis of the carbonylation of alcohols to carboxylic acids a detailed look at the Monsanto process. 

A good method for the direct conversion of alcohols to carboxylic acid uses 2,2,6,6-tetramethylpiperidin-l-oxyl (TEMPO) 51, in conjunction with the co-oxidant sodium chlorite (NaC102) and sodium hypochlorite (NaOCl) as a catalyst. See M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J. J. Grabowski and P. J. Reider, J. Org. Chem., 64 (1999), 2564. 

Oxidahon of alcohol to carboxylic acid + 1 Little change Introduction of acidic function. pK 3-5, reduction of log of 3-5 units... 

Reaction time has to be as short as possible in order to suppress side reactions. Especially the conversion of alcohols to carboxylic acids with one more C-atom, which will be discussed subsequently, or formation of ethers and free acids may be undesirable reactions [504]. The carbonylation rate of olefins with carbon monoxide/ROH in the presence of Co carbonyls can be accelerated remarkably by addition of small portions of hydrogen to carbon monoxide, which favors the formation of hydrocarbonyl. The same effect can be achieved by addition of pyridine. 

Scheme 23 Conversion of alcohols to carboxylic acids with water as the oxygen source, catalyzed by a Ru complex. ...

Balaraman E, Khaskin E, Leitus G, Milstein D. Catalytic transformation of alcohols to carboxylic acid salts and H2 using water as the oxygen atom source. Nat Chem. 2013 5 122-125. 

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