Synthesis of aspirin

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Aspirin is most widely sold over-the-counter drug. It has the ability to reduce fever (an antipyretic), to reduce pain (an analgesic), and to reduce swelling, soreness, and redness (an anti-inflammatory agent). Much of this is believed to be due to decreased production of prostaglandins and thromboxanes. Aspirin’s ability to suppress the production of prostaglandins and thromboxanes is due to its irreversible inactivation of the cyclooxygenase (COX) enzyme. Cyclooxygenase is required for prostaglandin and thromboxane synthesis.

Aspirin acts as an acetylating agent where an acetyl group is covalently attached to a serine residue in the active site of the COX enzyme. The synthesis of aspirin is classified as an esterification reaction. Salicylic acid is treated with acetic anhydride, an acid derivative, causing a chemical reaction that turns salicylic acid’s hydroxyl group into an ester group (R-OH > R-OCOCH3). This process yields aspirin and acetic acid, which is considered a byproduct of this reaction. Small amounts of sulfuric acid (and occasionally phosphoric acid) are almost always used as a catalyst.

This method is commonly employed in undergraduate teaching labs. Formulations containing high concentrations of aspirin often smell like vinegar because aspirin can decompose through hydrolysis in moist conditions, yielding salicylic and acetic acids. The acid dissociation constant (pKa) for acetylsalicylic acid is 3. 5 at 25°. Chemical Reactions Discussion of Results 3 grams of Salicylic Acid is equal to 0. 0217 mol of the compound. The stoichiometric relationship between Salicylic Acid and Acetylsalicylic Acid is 1:1 therefore the moles of Acetylsalicylic Acid (Aspirin) is 0.

0217 mol. In the overall reaction, 3 grams of Salicylic Acid will theoretically yield 3. 909 grams of Aspirin. 3g S. A. x (1mol S. A. /138. 118g) x (1mol A. A. / 1mol S. A. ) x (180. 15g A. A / 1mol A. A. ) = 3. 909 g Aspirin The measured weight of Aspirin in the experiment is 3. 5267 grams. The percentage yield is 90. 48%. Large amount of Aspirin was yielded but it is only an impure Aspirin this will lessen when recrystallization takes place. (3. 5267 g / 3. 9092g) x 100% = 90. 48%.

We use cookies to give you the best experience possible. By continuing we’ll assume you’re on board with our cookie policy Purpose: To synthesize aspirin, a common analgesic drug, via nucleophilic acid-catalyzed substitution reaction of salicyclic acid with acetic anhydride. …

We use cookies to give you the best experience possible. By continuing we’ll assume you’re on board with our cookie policy Aspirin is prepared by the esterification of salicylic acid with acetic anhydride under acidic conditions. The phenol group in …

We use cookies to give you the best experience possible. By continuing we’ll assume you’re on board with our cookie policy Introduction: The purpose of this lab was to demonstrate the ability to easily alter the molecular structure of a …

We use cookies to give you the best experience possible. By continuing we’ll assume you’re on board with our cookie policy The purpose of this lab was to learn how to use salicylic acid to make aspirin. Aspirin is the …

We use cookies to give you the best experience possible. By continuing we’ll assume you’re on board with our cookie policy The Preparation of Aspirin The purpose of this experiment is to synthesize aspirin (acetyl salicylic acid) from salicylic acid …

We use cookies to give you the best experience possible. By continuing we’ll assume you’re on board with our cookie policy Abstract Acetylsalicylic acid was prepared using salicylic acid and acetic anhydride. As a result, a white, powdery substance was …

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