Oxidative cleavage of unsaturated carbonyl compounds by alkali melts

Oxidative cleavage of unsaturated carbonyl compounds by alkali melts 

This method of oxidative cleavage is thus useless for determining the structure of olefins. Preparatively, however, it is often very valuable, as when nonanoic acid is obtained from the readily accessible 10-undecenoic acid  

Nonanoic acid 109 10-Undecenoic acid (1 part) and potassium hydroxide (3-4 parts) are heated in an iron vessel with a little water, the solids dissolving. Heating is continued with stirring until no more steam is evolved, then the temperature is raised so that the mixture becomes wholly fluid appreciable amounts of hydrogen are then evolved during 2-3 h. After cooling, the melt is dissolved in water, solids are filtered off, and the filtrate is acidified warm with hydrochloric acid. The precipitated oil is washed with water, then this crude acid is distilled in a vacuum, affording a moist forerun and then quite pure nonanoic acid, b.p. 186°/100 mm, m.p. 12.5°. 

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