Abstract
Abstract and summaryThe use of phase transfer catalysis (PTC) as an aid in the oxidation of long chain olefins with aqueous potassium permanganate (KMnO4) in neutral and alkaline media and with aqueous ruthenium tetroxide (RuO4) is reported. The phase transfer catalysts (PTCT) were either quaternary ammonium halides or crown ethers. The long chain olefins studied were 1‐pentadecene, 9‐octadecene, and methyl oleate. PTC not only increases the rate of these reactions but also gives good yields of reaction products. For example,cis‐9‐octadecene in methylene chloride reacted with aqueous KMnO4 to give either dihydroxyoctadecane (80%) or pelargonic, acid (80%) depending upon pH, when tetrabutylammonium bromide was used as the PTCT. When RuO4 in conjunction with a PTCT was used as the oxidant, a quantitative yield of myristic acid was obtained from 1‐pentadecene. The RuO4 oxidant was conveniently regenerated in situ from RuO2 and sodium hypochlorite. This regeneration is facilitated with a PTCT.
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