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Synthesis of a kairomone and other chemicals from cardanol, a renewable resource
(2012-06-05) Mmongoyo, Juma A.; Mgani, Quintino A.; Mdachi, Stephen J. M.; Pogorzelec, Peter J.; Cole‐Hamilton, David J.
Synthesis of a tsetse ﬂy kairomone component (3-propylphenol), a detergent [sodium 2-(dec-8-enyl)-6hydroxybenzenesulfonate], a polymer additive (1-octene), and a detergent precursor [3-(non-8enyl)phenol] using cardanol [3-(pentadec-8-enyl)phenol], has been accomplished. Both carbon– carbon double bond isomerization and metathesis methodologies were employed in the syntheses of these target molecules. The kairomone component was obtained, albeit in low yield, in three steps starting with cardanol. Synthesis of a new detergent, sodium 2-(dec-8-enyl)-6-hydroxybenzenesulfonate, was achieved by direct metathesis of cardanol with cis-2-butene followed by sulfonation and basiﬁcation. Finally, synthesis of 1-octene and 3-(non-8-enyl)phenol was accomplished in one pot by direct metathesis of cardanol with ethylene. These products have been characterized spectroscopically, especially using 1H and 13C NMR.