Macrocycle compounds derived from o-vanillin are compounds that belong to a group called Schiff bases. They are derived by the condensation of dialdehydes precoursors and p-phenylenediamine. Dialdehydes precoirsors are prepared by reaction of o-vanillin with α,ꞷ-dibromalkene on elevated temperatures in DMF as a solvent. The Schiff macrocyclic base is formed in mildly acidic solution of methanol and acetic anhydride. The pH conditions of the medium in which they are formed are crucial for the formation of Schiff bases. For the condensation of the o-vanillin and p-phenylenediamine in macrocyclic Schiff base to be successful it is necessary to use a medium whose pH is in 3-5 on pH scale range and elevated temperature. Acidic reaction conditions are required to eliminate \( H_{2}O\) and at the same time they must not be too acidic because the amine would be protonated, which would reduce nucleophilicity on the nitrogen atom. A decrease in the amine nucleophilicity would inhibit the first stage of the reaction. By forming the Schiff base, the C=O bond of the aldehyde is replaced by the C=N of the newly formed substituted imine. In this final paper, six compounds were synthesized- three of which are dialdehydes required for the synthesis three macrocycle Schiff bases. Synthesized products were weight and analyzed by FT-IR spectroscopy.