Ester Formation—Preparing Benzocaine

Monika Rizk
216 Section 318
Experiment 3
2/24/11
 Experiment 3: Ester Formation—Preparing Benzocaine

Introduction

Ethyl p-aminobenzoate, commonly known as Benzocaine, is a local anesthetic

found in many medications. It is primarily used to treat pain associate with various types

of burns, skin punctures, and insect bites. In this experiment, Benzocaine was synthesized

by the esterification of p-aminobenzoic acid with anhydrous ethanol in the presence of

catalytic sulfuric acid. The product was then characterized and analyzed using TLC, IR,

and melting point.

Reaction

Table

Compound Molecular Weight Amount mmoles Molar Equivalents

p-aminobenzoic acid 137 g/mol 0.360 g 2.63 1
Ethanol 46 g/mol 3.60 mL 6.18 2.35
H2SO4 98 g/mol 0.3 mL 5.63 2.14
Benzocaine 165 g/mol --- 2.63 1
Procedure

0.360 g of p-aminobenzoic acid was combined with 3.6 mL of excess ethanol in a

10 mL conical flask. The flask was placed in a sand bath on the stir plate with a magnetic

spin vane and stirred until the solid acid dissolved. 0.3 mL of concentrated sulfuric acid

was added dropwise while the solution was stirring and a white precipitate formed. A

water-cooed condenser was attached to the flask to prevent vapor loss and the solution

was heated until it boiled for about 65 minutes. After the reaction reached completion, it

was cooled to room temperature. Using a Pasteur pipet, the solution was transferred to an

Erlenmeyer flask containing 3 mL of water. The solution dissolved in the water and 10%

sodium carbonate was added dropwise until CO2 was no longer released and precipitate

was forming. Suction filtration was used to collect the crude product and the product was

then recrystallized. The purified product was finally analyzed using TLC, IR, and melting

point.

Results

***Individual product did not yield—required to use Elizabeth Demonte’s experimental

data.

Yield
Compound Theoretical Yield Actual Yield Percent Yield
Pure Benzocaine 0.434 g 0.05 g 11.5%

Melting Point
Compound Melting Point
Pure Benzocaine 77.1ºC

TLC
Compound Rf Value
p-aminobenzoic acid 0
Benzocaine 0.4

IR: See attached IR spectra.

Discussion

The individual product did not yield the final product of Benzocaine due to issues

neutralizing the reaction with sodium carbonate. Because of this, Elizabeth Demonte’s

experimental data was used for characterization and analysis.

After analyzing the results, it was concluded that p-aminobenzoic acid was

converted to a chemically different compound. The recorded co-spot on the TLC plate

comparing p-aminobenzoic acid and the product, Benzocaine, confirmed this finding.

The Rf values of the compounds were quite different, which correlates to the different

polarities of the compounds. p-aminobenzoic acid had a lower Rf value than did the end

product, which directly corresponds to the fact that carboxylic acids are more polar than

esters, like Benzocaine.

The product was subject to a melting point test and the product melted at about

77.1ºC. The projected melting point of Benzocaine is about 92ºC. The recorded melting

point of the formed product was lower by about 15ºC, which could be attributed to water

contamination in the pure product. The presence of water in the product would cause the

melting point to be lower than expected. By allowing the product to dry for a longer

period of time and then performing another melting point test, this would mostly like

result in more accurate data.

An IR spectrum was taken for the Benzocaine product and compared to an official

IR spectrum of Benzocaine and p-aminobenzoic acid (SBDS). The recorded Benzoic

product had a peak around 2980 cm-1, corresponding to the sp3 C-H stretch in the ester.

This peak was not present in the IR spectrum of p-aminobenzoic acid, confirming that the

product acquired C-H bonds, correlating to the structure of Benzocaine. The IR spectrum
of p-aminobenzoic acid showed a peak around 3000 cm-1, which is the O-H stretch of a

carboxylic acid. This peak was not found on the IR of Benzocaine, confirming the

esterification took place. The recoded IR spectrum of Benzocaine was compared to the

official IR of Benzocaine found online and the two spectra showed similarities both

qualitatively and quantitatively. This further confirms that Benzocaine was successfully

produced.

The percent yield of Benzocaine was 11.5%. This error could be attributed to

water contamination and the transfer of solution through many reaction vessels. Another

potential cause for error could be due to the starting carboxylic acid not being fully

dissolved in the ethanol.

Conclusion

Although the individual experiment did not result in a successful yield of

Benzocaine, Elizabeth Demonte’s experimental data confirmed that the p-aminobenzoic

acid was converted to Benzocaine. This was confirmed by analyzing and characterizing

the data of the produced Benzocaine. The recorded TLC plate proved the starting

compound was more polar than the final product due to corresponding R f values. This

data corresponds to the known polarities of carboxylic acids and esters. The melting point

of the product was also compared to the known melting point of Benzocaine. Finally, IR

spectra confirmed that Benzocaine was in fact produced. Certain functional groups

vanished and appeared in the starting acid and in the product, which confirms the

structure of the compounds.