Synthesis and Analysis of Benzyl Acetate

Alexandra Zambanini

Introduction

Condensation reactions between alcohols and anhydrides are very important in that they

lead to the synthesis of esters. Esters are important from a chemist’s viewpoint due to their

ability to form other esters, amides and carboxylic acids.

Benzyl acetate was synthesized in this experiment through the esterification of benzyl

alcohol using acetic anhydride. It is a low molecular weight ester, which means it has a

characteristic aroma, in this case of jasmine, peach and pear. This property of benzyl acetate

leads to its extensive use in many perfumes, cosmetics, soaps and various household items that

are meant to exude these specific fragrances.

Another importance use of benzyl acetate is demonstrated in apiology. Male orchid bees

are attracted to the sweet smelling benzyl acetate, which is a major component in the essential

oils of many flowers. The bees use benzyl acetate to synthesize vital pheromones, but more

importantly benzyl acetate can be used as enticement to attract the bees so that they can be

gathered for research.

The purpose of this experiment was to synthesize and analyze benzyl acetate. The study

incorporated Thin Layer Chromatography (TLC) to monitor the reactions progress. The product

was isolated and purified via extraction techniques and the use of a separatory funnel. Nuclear

Magnetic Resonance (1H-NMR) and Infrared (IR) spectroscopy were used to analyze the final

product.
Experimental

Benzyl alcohol (540 mg, 4.99 mmol) and acetic anhydride (510 mg, 4.99 mmol) were

added to a 25 mL round-bottomed flask equipped with a boiling chip. A distilling column was

attached to the top of the flask. The apparatus, containing the reactants, was placed in a sand

bath and allowed to reflux for approximately one hour and twenty minutes. The resulting

mixture was cooled to room temperature and wet ether (1 mL) was added to it.

TLC analysis was then performed to determine if product had formed. The mobile phase

employed was 50:50 hexanes/dichloromethane. Spots included benzyl alcohol, the reaction

mixture and a co-spot including benzyl alcohol and the reaction mixture. The results showed

that the reaction mixture contained little trace of benzyl alcohol, the more polar compound, and

was almost entirely product, so extraction and purification procedures ensued. Water (1 mL)

was added to the mixture and the organic layer was separated using the separatory funnel. The

resulting aqueous layer was washed with ether (1 mL) and the organic layer was separated using

the same technique. The ether layers obtained were then combined and washed with sodium

bicarbonate (1 mL), water (1 mL) and saturate sodium chloride (1 mL). The ether layer was then

dried using excess anhydrous sodium sulfate, then decanted into a shorty vial. The ether was

evaporated using a stream of nitrogen.

Benzyl acetate was isolated as a clear, colorless liquid with a strong fruity odor similar to

the aroma of a peach. 1H-NMR and IR spectrum were then obtained to analyze the purity of the

product.

Table 1: 1H-NMR Data for Benzyl Acetate, Obtained using Deuterated Chloroform Solvent on a

60 MHz NMR.
 Significant Signals

Integration Value Splitting Pattern Position (ppm)

A 3H Singlet 2.1

B 2H Singlet 5.1

C/D/E 5H Complex multiplet 7.6

Table 2: IR Data, Obtained by Compressing the Benzyl Acetate on the Diamond Surface of the

Solids/Liquids IR instrument.

Significant Signals

Observed Bond Stretch

2800-3200 C-H

1735.1 C=O

1224 C=C

Results, Discussion and Conclusions

The results in Table 1 proved the identity and demonstrated the purity of the product,

benzyl acetate. Looking at Figure 1 (appendix), the 1H-NMR data, it is clear that three

significant peaks were observed. Peak A, a singlet at 2.1 ppm, indicates the presence of the

methyl group attached to a carbonyl. Peak B, a singlet at 5.1ppm, indicates the presence of the

methylene group attached to a benzene ring. Peaks C, D and E for a complex multiplet at 7.6

ppm, due to equivalency of the hydrogens, and indicate the presence of an aromatic ring. These

results correspond with those expected for benzyl acetate.

 Another method used to analyze the product was IR spectroscopy. The results in Table 2

and Figure 2 (appendix) show three significant peaks at 1224, 1735.1 and 2800-3200 . The

peak at 1224 accounts for the C=C stretch due to the aromatic ring. The peak at

1735.1 accounts for the C=O stretch due to the carbonyl. The peaks from approximately

2800-3200 account for the C-H stretches. The C-H stretch from 2800-3000 is likely

due to the vibrations of bonds of hydrogen and hybridized carbon atoms in the molecule,

while the C-H stretch from 3000-3200 is likely due to the vibrations of bonds of hydrogen

and hybridized carbon atoms of the aromatic ring. These results looked promising since they

coincided with those expected for benzyl acetate.

In conclusion, the synthesis of benzyl acetate proceeded successfully, proving this

method of alcohol esterification is very efficient and practical in producing esters. Expected

results for 1H-NMR and IR spectrums of benzyl acetate were obtained for the crude product with

very minimal deviation, proving that very pure benzyl acetate was synthesized.

References

Minard, B.; Masters, K.M.; Bortiatinski, J.; Halmi, T.; Williamson, K. “Lab Guide For

Chemistry 203 & 213B”, 2009-2010 pp.277-319

Schiestl, F.P. & Roubik, D.W. (2004). "Odor Compound Detection in Male Euglossine Bees",

Journal of Chemical Ecology, 2004 pp.253–257

Williamson, K. L. “Macroscale and Microscale Organic Experiments” Second Edition 1994,

Houghton Mifflin, Boston p. 385; revised 10/18/06