Alcohols, primary with sodium permanganate

In nonaqueous media, the oxidation of alcohols to acids is accomplished in heterogeneous systems by refluxing primary alcohols with solid sodium permanganate monohydrate in hexane (equation 232). The reaction is applicable even to allylic alcohols [555]. 

Ogawa later published the synthesis of a 3-amino-3,4-dideoxyhexiu-onic acid in route to ezomycin [24]. In that account, a 1,6-anhydro epoxy sugar was reacted with sodium azide followed by antimony pentachloride to give methyl 3-azido-2-0-benzoyl-a-D-glucospyranoside. Oxidation of the primary alcohol was achieved with potassium permanganate, and reduction of the azide was accomplished with hydrogenation (Fig. 8). 

Carbons that are already partially oxidized such as alkenes, primary alcohols, aldehydes, and methyl ketones are more readily oxidized to the carboxylic acid. Appropriately substituted alkenes may be cleaved using ozone followed by treatment with hydrogen peroxide to give carboxyUc acids. A convenient alternative is the combination of sodium periodate and a catalytic amount of permanganate (Eq. 6.2) [4]. The permanganate... 

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