The reaction steps involved in the synthesis of benzocaine from p-nitrotoluene is in the following order
Oxidation - Esterification - Reduction
Reduction - Oxidation - Esterification
Oxidation – Reduction - Esterification
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Benzocaine is the trade name for the local anesthetic known chemically as ethyl p-aminobenzoate, which is found in many creams and ointments used in the treatment of pain due to sunburn, minor burns, cuts, scrapes and insect bites. Benzocaine is structurally analogous to Cocaine, Lidocaine, and Novocaine (shown below) and is prepared by the esterification of p-aminobenzoic acid with ethanol.1 Note that esterification reactions can be significantly influenced by the concentration of starting materials and products in solution, as explained by Le Chatelier’s Principle.
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1. Salkaowski Ber. 1895, 28, 1921 and Adams, Cohen, Org. Syn. Coll. Vol. I, 2nd ed., 1932, p. 240
Reaction Scheme
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