Synthesis of chloroalkoxy eicosanoic and docosanoic acids from meadowfoam fatty acids by oxidation with aqueous sodium hypochlorite

Chloroalkoxy substituted C-20 and C-22 fatty acids can be synthesized from the unsaturated fatty acids in meadowfoam oil by reaction of the fatty acid s with primary or secondary alcohols and an aqueous sodium hypochlorite sol ution (commercial bleach). The reactions are conducted at room temperature for 3 h. Chlorohydroxy fatty acid derivatives are formed as by-products owi ng to the presence of water in the reaction mixture. Chlorinated delta-lact ones are also produced by direct reaction of sodium hypochlorite with the D elta 5 unsaturated fatty acids present in meadowfoam or by ring closure of the 6-chloro-5-hydroxy fatty acids. The product yield of chloroalkoxy fatty acids is dependent on the nature and volume of the alcohol used in the rea ction, as well as the concentration and pH of the sodium hypochlorite solut ion. Primary alcohols such as methanol and butanol produce maximal yields ( 50-60%) of chloroalkoxy fatty acids whereas the secondary alcohol 2-propano l gives a 30% yield. Chloroalkoxy fatty acid yields can be increased to 75- 80% by elimination of water from the reaction mixture through a procedure t hat partitions sodium hypochlorite from water into hexane/ethyl acetate mix tures. All of the reaction products were fully characterized using nuclear magnetic resonance and gas chromatography-mass spectrometry.