Oxidation with Sodium Periodate and Potassium Permanganate

OXIDATION WITH SODIUM PERIODATE AND POTASSIUM PERMANGANATE 

A mixture of 0.2824 g (1 mmol) of oleic acid, 0.414 g (3 mmol) of potassium carbonate, 1.712 g (8 mmol) of sodium metaperiodate, and 0.021 g (0.134 mmol) of potassium permanganate in 400 mL of water is kept at 20 C for 20 h. The solution is strongly acidified with 10% sulfuric acid and extracted with ether. Evaporation of the extract gives 0.354 g of a residue, which on trituration with petroleum ether gives 0.161 g of oily pelargonic acid and 0.193 g of crystalline azelaic acid, mp 102-104.5 °C. Pure pelargonic acid is obtained by vacuum distillation, and pure azelaic acid (mp 106.5-107.5 °C), by recrystallization, first from water and then from ethyl acetate. Yields of both crude acids are quantitative, but the yields of purified products are not stated. 

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