General Procedure for Oxidation of Alcohols with Fetizons Reagent

General Procedure for Oxidation of Alcohols with Fetizon s Reagent 

From 1 to 10 g (ca. 5-15 equivalents)—typically 3 g—of silver carbonate on Celite per mmol of alcohol are added to a ca. 0.01-0.15 M solution of the alcohol in drya benzene.b The resulting suspension is refluxed till most of the starting alcohol is consumed.0 The suspended solid is filtered, employing filter paper or a pad of Celite , and washed with benzene or other organic solvent. Concentration of the organic solution at the rotary evaporator yields the crude carbonyl compound that may need further purification. 

An alcohol is oxidized with Fetizon s reagent in the presence of a very oxidation-sensitive dialkoxy alkene that, for instance, suffers selective cleavage with no reaction on the alcohol moiety on contact with PCC. 

The oxidation of this alcohol can be carried out employing Fetizon s reagent under simple experimental conditions with quantitative yield. Alternatively, a Swem oxidation can be used resulting in 92% yield. 

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