A 3- Step Synthesis of 3,4-Dihydro-3-(p-methylphenyl)-1,3,2H Benzoxazine

A three step synthesis was done to create 3,4-DiHydro-3-(p-methylphenyl)-1,3,2H Benzoxazine, which is found in biological molecules. In the first step, salicylaldehyde and p-toluidine were reacted to create salicylal-p-toluidine. In the second step, this product was added to sodium borohydride to form N-(2-hydroxybenzyl)-p-toluidine. For the final step, the product in step two was added to a solution of paraformaldehyde and potassium hydroxide to create the final product of 3,4-DiHydro-3-(p-methylphenyl)-1,3,2H Benzoxazine. The purpose of the experiment was to determine how effective the use of a “greener” solvent would be. In order to do this, the solvent, ethanol, was used to replace methanol, the suggested solvent. The product of each step was confirmed by infrared analysis (IR), nuclear magnetic resonance spectroscopy (NMR) and melting point.