Alcohols, allylic with permanganates

The chloride is prepared by the action of dilute hydrochloric acid upon the iiitrate, or by using potassium chloride and carbon dioxide. When treated with moist silver oxide it yields an aqueous solution of the hydi oxide, the latter also being formed when freshly precipitated mercuric oxide, allyl alcohol, and water are shaken together. Reduction of the chloride by zinc and hydrochloric acid gives an odour of allyl alcohol, whilst oxidation with permanganate causes the immediate decomposition of the compound mth the formation of oxalic acid. 

The impurities of propylene carbonate that have been identified by gas chromatography85 include C02, water, propylene oxide, allyl alcohol, 1,2-propylene glycol, 1,3-propylene glycol, and lesser amounts of unidentified materials. The solvent may be purified readily by vacuum fractional distillation, with a reflux ration of 10 1 at 0.5-1 torr. At this pressure the column head temperature is 72-75°C. Another suggestion is to heat propylene carbonate with sodium carbonate and potassium permanganate (both 10 g L 1) for 2 h prior to vacuum distillation. 

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]. 

Similar results are obtained with copper permanganate octahydrate, Cu(Mn04)2 8H20. Addition of this salt to a solution of 2-decanol in di-chloromethane results in an exothermic reaction and boiling of the mixture for 5 min. After 10 additional minutes at room temperature, 2-decanone is isolated in 93% yield [894. Allylic alcohols are oxidized in 84-85% yields to a, 3-unsaturated ketones after boiling in dichloromethane for 24 h [894]. 

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