Preparation+of+Eugenol+Benzoate
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Preparation+of+Eugenol+Benzoate

Course Number: CHEM 3361 LAB, Spring 2008

College/University: Kennesaw

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Preparation of Eugenol Benzoate1 Eugenol (4-allyl-2-methoxyphenol) can be easily isolated from cloves. 2 In order to aid in the identification of this natural product, eugenol can be reacted with benzoyl chloride to produce a solid, eugenol benzoate. A melting point may be obtained to confirm that the desired product was produced and therefore, that eugenol was isolated. This method of indirect characterization of...

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of Preparation Eugenol Benzoate1 Eugenol (4-allyl-2-methoxyphenol) can be easily isolated from cloves. 2 In order to aid in the identification of this natural product, eugenol can be reacted with benzoyl chloride to produce a solid, eugenol benzoate. A melting point may be obtained to confirm that the desired product was produced and therefore, that eugenol was isolated. This method of indirect characterization of an organic molecule by characterizing a solid derivative has been widely used in the past, but has been superceded by modern spectroscopy (i.e. nuclear magnetic resonance, infrared spectroscopy, mass spectrometry, etc.) OCH3 OH O Cl KOH, H2O OCH3 O O eugenol benzoyl chloride eugenol benzoate mp 70oC This reaction will be performed on a very small scale for two reasons. First, in a modern scientific lab, experiments are often carried out on as small as a few milligrams of starting material or a microscale. It is very important that you develop the skills needed to complete microscale reactions and obtain a high yield after all you don't have much to loose. Second, the quantity of eugenol benzoate need only be sufficient to perform an IR and m.p. to help characterize the eugenol that you isolated. Therefore, there is no need to produce large quantities that would only be placed in the waste. Procedure Place about 0.20 g of eugenol (or clove oil) in a small test tube and add 1 mL water. Add 5% aqueous KOH until oil dissolves (may not be completely clear). To this solution, add 4 to 5 drops of benzoyl chloride while holding the tube in a fume hood. Stopper and shake the mixture. Remove the stopper. Warm the reaction for 5 minutes on a heating mantle set at 30 V. Cool the tube a in beaker of cool water. Once at room temperature, add 2 mL ether and shake to mix layers. Remove the lower, aqueous layer from the tube with a pipet. Add a small amount of sodium sulfate to dry the remaining ether layer. Filter the ether layer through a plug of cotton or glass wool into another test tube. Add 1 mL of methanol. Evaporate the solution to about 0.5 mL and cool in a beaker of ice water in order to crystallize the product. Collect the crystals and allow to dry. Determine the melting point. Caution: avoid breathing benzoyl chloride vapors, avoid skin contact with benzoyl chloride 1 2 Rodig, O. R.; Bell, C. E. Jr.; Clark, A. K. Organic Chemistry Laboratory: Standard and Microscale Experiments, Saunders College Publishing: New York, 1990, pp. 123-124. Ault, A. Techniques and Experiments for Organic Chemistry, 6th edition; University Science Books: Sausalito, California, 1998, pp. 344-347. Notebook Note: The preparation of eugenol benzoate is the first of several organic reactions we will perform in Organic Chemistry I Lab. For each of these synthesis experiments, you are required to write the reaction and provide a table of quantities in both your notebook. An example is shown below. You should complete as much of the table as possible prior to coming to lab and record actual quantities during lab. O OH Cl O KOH H2O O O O Name Molecular Formula Eugenol C10H12O2 etc. Molecular Weight (g/mol) 164.20 Amount (theo.) (actual) Moles (theo.) (actual) 0.20 g 0.22g 0.0012 0.0013 bp 254 C mp 70 C >>> Reaction and text in bold in the table above must be written in lab notebook before pre-lab. Text not in bold should be your actual amount recorded during lab.

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