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Synthesis of Aspirin2

Synthesis of Aspirin2

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Published by Kunjal
acetic anyhdride and acetanilide
acetic anyhdride and acetanilide

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Published by: Kunjal on May 21, 2010
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Synthesis of Aspirin (Acetylsalicylic Acid) Kunjal Patel TA: Scott Plunkett May 18, 2010 Purpose: To prepare acetylsalicylic acid via

synthesis of salicylic acid and acetic anhydride.

Procedure: 1 In a conical vial salicylic acid (0.210g, 1.52mmol), acetic anhydride (0.480ml, 0.519g, 5.08mmol) were added and concentrated phosphoric acid (1 drop) as a catalyst was added to the vial. The vial was partially submerged in a (50 °C) hot water bath. The mixture in the vial was stirred until the dissolution of solid. The vial was cooled to room temperature (23°C). Once the crystals were evident in the solution the vial was further cooled in ice water bath for complete crystallization. The crystals were isolated using vacuum filtration technique to yield white crystalline of acetylsalicylic acid (0.2143g, 1.189mmol, 78.2%): mp 128°C (lit2 134-136 °C). Discussion: The synthesis of Acetylsalicylic acid using salicylic acid and acetic anhydride under basic conditions yielded 78.2% white crystalline solid. The melting point of the pure product was determined to be 128°C, This could have some effect on the purity, for the melting point of the harvested acetylsalicylic acid was not close to the literature melting point Since the final product was determined not to be very pure, it is highly likely that less than 0.2143g of the product was acetylsalicylic acid. Further analysis of the product will have to be done to determine exactly how pure the product actually was. There were several problems that could have contributed to the low purity. When dissolving the initial amount of salicylic acid in the solution of acetic anhydride and concentrated phosphoric acid, it did not completely dissolve into the solution, even when it was heated. This could have a slight impact on the results of the overall yield of aspirin because it was possible that not all of the salicylic acid was synthesized. To determine if this affected the synthesis of aspirin at all, the experiment should have been ran a second. And the iron (III) chloride test also could have been ran to determine if any of the aspirin degraded to salicylic acid or never converted from salicylic acid3. Another approach to synthesize aspirin would be using CaCO3 with microwave irradiation during this procedure use of Brønsted bases as catalysts with microwave irradiation improved the yield, and reaction time. This seems contradictory because traditional

synthesis involves Brønsted acid as catalyst for higher yield and reaction time because of the nature of the leaving group in the reaction mechanism another way to improve yield was when synthesizing aspirin with microwave irradiation without the use of catalyst seemed to produce the highest yield (80%) and the reaction was completed within 10-13minutes4. By omitting the use of solvents for recrystallization in the previous procedures we can also introduce the solvent-free principle and introduction to green chemistry. __________________________________

1 Paul,N. Organic Chemistry Lab – Chemistry 254; McGraw‐Hill: New York, 2009; pp 155–162. 2 Sigma-Aldrich Chemical Catalog Online. http://www.sigmaaldrich.com/unitedstates.html (accessed May 2010); Search: Product No. 132926. 3 Susan Baker. University of Main at Augusta. http://faculty.uma.edu/sbaker/chy%20106%20asa.htm accessed May 2010. 4 David Sanabria, Marilyn García, Joaudimir Castro, and Johanna Fajardo. University of Puerto Rico, http://test.scheikundeinbedrijf.nl/content/Modules/Modulenaam/Files/p628.pdf accessed May 2010.

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