Mgaya, James E.Mubofu, Egid B.Mgani, Quintino A.Cordes, David B.Slawin, Alexandra M. Z.Cole‐Hamilton, David J.2016-06-152016-06-152014-09Mgaya, J.E., Mubofu, E.B., Mgani, Q.A., Cordes, D.B., Slawin, A.M. and Cole‐Hamilton, D.J., 2015. Isomerization of anacardic acid: A possible route to the synthesis of an unsaturated benzolactone and a kairomone. European Journal of Lipid Science and Technology, 117(2), pp.190-199.http://hdl.handle.net/20.500.11810/2455Full text can be accessed at http://onlinelibrary.wiley.com/doi/10.1002/ejlt.201400268/fullCrystalline unsaturated lactone, 8-hydroxy-3-tridecyl-1H-isochromen-1-one (6) has been synthesized by isomerization of anacardic acid having heterogeneous alkyl side chains (a mixture of mono-, di-, and tri-unsaturated anacardic acid) (1). Hydrogenation of 8-hydroxy-3-tridecyl-1H-isochromen-1-one produced a saturated lactone, 8-hydroxy-3-tridecyl-3,4-dihydroisochromen-1-one (7). Isomerization of monoene anacardic acid resulted in a crystalline isoanacardic acid, (E)-2-hydroxy-6-(pentadec-1-enyl)benzoic acid (8) as a major product. This was then metathesized with 2-butene to give 3-prop-1-enylphenol (10). Both isomerization reactions used a 1,2-bis(ditertiarybutylphosphinomethyl)benzene modified palladium catalyst. The two products, 8-hydroxy-3-tridecyl-1H-isochromen-1-one and (E)-2-hydroxy-6-(pentadec-1-enyl)benzoic acid have been crystallographically characterized.enAnacardic acidBenzolactoneDouble bond isomerisationIsoanacardic acidKairomoneJournal Article10.1002/ejlt.201400268