Multi-Step Synthesis of Benzocaine

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CHEM360 Experiment 17 Report Date: 3 June 2012 Student Name: Colin L Evans ID Number: 2990817 Title: Multi-step Synthesis of Benzocaine Objective(s): The primary objective of this experiment is to provide a practical example of the synthesis of an organic compound over the course of multiple steps. Reaction equation(s): Introduction: Throughout this organic chemistry course there have been several theoretical questions on how to make a certain organic compound from basic material. All questions assume that one has access to unlimited reagents and also assumes away the time required to perform these multiphase synthesises. This experiment is an actual example of the synthesis of an organic compound from basic material. The ultimate goal of this experiment is to synthesize benzocaine from p-nitrotoluene. In order to achieve this, the following multiple steps will be employed: 1. The reduction of p-nitrotoluene to create p-methylaniline. The reducing agent for this phase is a metal –acid combination, tin and hydrochloric acid. 2. Acetylation of p-methylaniline to create p-methylacetanilide. Here acetic anhydride will be used to prepare the nitrogen substituted acetamide. This is conducted to make the amine group, which is a very stong ortho and para directing activator on an aromatic ring, a lesser strength activator so that the oxidation of the methyl group can proceed. 3. Oxidation of p-methylacetanilide. Here the methyl group on p-methylaniline is oxidized with potassium permanganate to transform the methyl group into a carboxyl-group and ultimate create p-acetamidobenzoic acid. 4. Hydrolysis of p-acetamidobenzoic acid will transform the amide group into an amine group and will create the amino acid p-aminobenzoic acid. Here the
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