Synthesis of Aspirin1

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Michigan State University *

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Chemistry

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Oct 30, 2023

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skin, eyes, and clothing. Avoid breathing the dust. Acetic anhydride is toxic, corrosive, and a lachrymator (causes tears). Wear gloves. Avoid contact and use in the fume hood. Sulfuric acid and phosphoric acid are corrosive and cause burns. Avoid contact. Dispose of the liquid residue in the liquid waste tank. Experimental Procedure Esterification 1. Place 1.0 g salicylic acid and a stir bar in a small beaker. 2. Add 2 mL of acetic anhydride carefully while stirring the mixture. 3. Add 5 drops, or 0.2 g, of your assigned catalyst. 4. After about 10 minutes, place the beaker in a hot water bath so that any remaining solid dissolves and the reaction goes to completion. 5. Pour the resulting solution into about 20 mL of ice water and wait for crystallization. 6. Vacuum filter and dry. This lab is adapted from Green Chemistry Laboratory Course (CEM 255) - Michigan State University. Melanie Cooper, Elizabeth Day, Mengqi Zhang . Post Lab Questions 1. Identify the limiting reagent and calculate the percent yield using the data your group collected. (1 pt)
2. How did you isolate your product after the reaction? How can addition of ice water assist with precipitation/crystallization? Should the aspirin product be a solid or liquid at room temperature? (2 pt) 3. Complete the following reaction by filling in the box. Include all products. (1 pt) 4. Which of the synthesis routes is the most economical? Use the price reference table below for calculation. (1 pt) Reagent Retailer price Retailer container size Salicylic acid $ 95.00 500 g Acetic anhydride $ 98.50 1 kg Sulfuric acid $ 107.30 2.5 L Phosphoric acid $ 328.00 500 mL γ -valerolactone $ 73.20 100 g
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