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Published by: Xiang Yu on Dec 06, 2012
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12/06/2012

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Benzocaine Synthesis via Fischer EsterificationXiang YuMarch 24
th
, 2012
 
Introduction
Synthesis of esters has played a significant role in Organic chemistry since its infancy. Theimportance lies in the utility of esters both in laboratory field and industry field. In laboratoryesters are important sources of corresponding amides. Also esters can be used to productketones and aldehydes. The essential feature of esterification reaction lies in its broadutilization in industry . Esters ranging from aliphatic to aromatic are generally used asplasticizers, solvents, perfumes, and flavor chemicals and also as precursors for pharmaceuticals, agrochemicals and fine chemicals. However, Fischer Esterification is not a perfect reaction in theindustry field. The use of traditional acidic catalyst such as sulfuric acid will cause side reactionsand corrosion of equipment and require removal large amount of salt waste during neutralizationof acid
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Recently a new type of acid catalyst called ionic liquid was invented to overcome theproblem.
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Esters generally have low melting point and low boiling point .Since esters lack hydrogen-bond donating hydrogen , the intermolecular force between the ester molecules arevery week. Many esters have aroma and this property has been used in production of essence.Benzocaine is a white solid which is generally used as a external- used anesthetic. Forexample, it can be used to relive pain due to the oral injection.
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It can also be used toanesthetize fresh- water fish
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. In this experiment, benzocaine will be synthesized by FischerEsterification of p-aminobenzoic acid with ethanol in an acidic condition.The mechanism of this reaction is involved in several steps. First, the startingmaterial p-aminobenzoic acid is activated by protonation of carbonyl oxygen. Second, thetetrahedral intermediate is formed by nucleophilic attack of ethanol on the p-aminobenzoic acid.In the third step transfer of a proton from one oxygen atom to another yields a second tetrahedralintermediate and converts the Hydroxyl group into a good leaving group. Finally, the loss of aproton from oxygen and expulsion of water regenerates the acid catalyst and gives the esterproduct benzocaine.
 
 Figure 1: Formation of bezocaine from p-aminobenzoic acidThe purpose of this experiment is to synthesis benzocaine by Fischer Esterification.Refluxing method to the reaction mixture will be used in the experiment in order to proceed theesterification reaction without decreasing the amount of solvent. To precipitate the product fromsolution, the PH of reaction mixture is made to eight. The product will be isolated by vacuumfiltration and washed by distilled water. 60 MHz
 
IR, GC ,GC-MS and melting pointanalysis were applied to identify the compound.

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