In this work, the new phthalonitrile derivative 3 bearing 4-pentylphenol 1, metal-free phthalocyanine 4, metallophthalocyanines 5 and 6 have been synthesized. Metal free phthalocyanine 4 and metallophthalocyanines 5 and 6 bearing four 4-(4-pentylphenoxy) groups on the periphery have prepared by cyclotetramerization of a new precursor, namely 4-(4-pentylphenoxy)phthalonitrile 3 in the presence of the corresponding divalent metal salts [Zn(II), Co(II)]. The new compounds have been characterized by IR, H-1 NMR, C-13 NMR and MS spectra data. The new cobalt phthalocyanine 6 has tested as a catalyst for the oxidation of cyclohexene with different oxidants, such as tert-butylhydroperoxide (TBHP), m-chloroperoxybenzoic acid (m-CPBA) and hydrogen peroxide (H2O2), in organic solvent. It is seen that complex 6 can selectively oxidize cyclohexene to give 2-cyclohexen-one as major product, 2-cyclohexenol and cyclohexene oxide as minor product. Finally, because of the minimal destruction of the catalyst, higher selectivity and conversion, TBHP has found to be best oxidant. (C) 2013 Elsevier B.V. All rights reserved.