The article describes the synthesis and extraction properties of a new chiral calix[4]arene Schiff base ligand 5, which has been synthesized from 5,17-diformyl-25,27-bis-(4-nitrobenzyloxy)-26,28-dihidroxycalix[4]arene (4) by treatment with (S)-(-)-1-phenylethylamine. In this synthesis, it was thought to explore the role of chiral, as well as Schiff base sites in the recognition of targeted species ions (such as dichromate anions) as well as neutral/chiral molecules. At low pH, the ligand 5 is more effective for transferring the dichromate anions from an aqueous into a dichloromethane layer; may be due to the protonation of nitrogen atoms. The extraction properties of ligand 5 towards the some selected α-amino acid methylesters are also reported. However, the ligand 5 did not display any selectivity towards the selected -amino acid methylesters.