benzocaine

Synthesis of Benzocaine, a Local Anesthetic
Jason Hoyos* and Garrett Oakley
Department of Chemistry
University of Florida
P.O. Box 117200
Gainesville, FL 32611-7200


November 24, 2003


Introduction:

Naturally occurring anesthetics have been used for over a decade to dull or alleviate the pain involved with medical procedures. The extract of coca leaves was the first to be used. Its active ingredient, cocaine, was effective, but its addictive tendencies caused it to be abandoned as an anesthetic and outlawed as a drug. Do to their greater effectiveness and decreased side effects, synthetic anesthetics are more commonly used today. Essential to the effectiveness of these anesthetics are the aromatic ring at one end and possibly a secondary or tertiary amine at the other end of the molecule, separated by a one- to four- unit hydrocarbon chain.
In this experiment, 4-aminobenzoic acid ethyl ester (1), commonly known as benzocaine, will be prepared from 4-(acetylamino...