Experiment No.

8
Acetylation of Salicylic Acid
1. Objectives(s):
To synthesize products commonly produce in different fields of chemistry
2. Intended Learning Outcomes (ILOs):
The students shall be able to:
2.1 Synthesize aspirin from acetylation of salicylic acid
2.1 Confirm the presence of aspirin through various confirmatory test employed
3. Discussion
The curative powers of the willow tree bark have been known for centuries. Studies on extracts of the
willow bark indicated that it is a pain reliever, a fever inducer, and an anti-inflammatory agent.
The active ingredient in willow bark, salicylic acid, was synthesized in 1853 by the French chemist
Charles Gerhardt. Unfortunately, many people experience serious side effects with salicylic acid. In 1893,
Felix Hoffmann, a German chemist, synthesized the acetyl derivative, acetylsalicylic acid. A few years later,
the Bayer Company began marketing acetylsalicylic acid under the trade name aspirin.
Salicylic acid contains a phenol group. The phenol group can react with acetic anhydride to form an ester,
as shown in Equation 1. Phosphoric acid is used to catalyze the reaction.

Over time, commercial aspirin reacts with moisture in air to hydrolyze into salicylic acid and acetic acid.
4. Materials:
Beaker Mortar and Pestle
Gooch Crucible Round Bottom Flask
Rubber Funnel Leighbig Condenser
Suction Flask Pipettes
Aspirator Spatula
Glass Rod Hot Plate
Graduated Cylinder Iron Stand
Thermometer Test Tube
Watch Glass Salicylic Acid
Acetic Anhydride Commercial Aspirin
Adjustable Clamp FeCl3 & Phosphoric Acid
5. Procedures:
Acetylation
1. Prepare a hot – water bath by placing approximately 400mL of water into a 600-mL beaker.
2. Assemble a reflux apparatus, as shown in Figure 1.
 3. Put 3.00g of salicylic acid into the round – bottom flask
4. Add 10mL of acetic anhydride.
5. Use a Pasteur pipet to add 5 drops of 85% phosphoric acid.
6. Reassemble the reflux apparatus without delay.
7. Place the reaction flask in the 50 degrees Celsius hot – water bath. Clamp the flask in place.
Turn on the stirrer.
8. Stir the reaction flask to dissolve the salicylic acid.
9. Once the salicylic acid has dissolved, continue heating the mixture for an additional 15
minutes.
Product Separation
1. Remove the reaction flask from the hot – water bath. Transfer the reaction mixture, while it is
still warm, to a 25 – mL beaker. Allow the reaction mixture to cool to room temperature.
2. Prepare an ice – water bath using the 250 – mL beaker. Put 10 mL of distilled or deionized
water into a large test tube. Chill the water in the ice – water bath.
3. If the product crystals have not appeared, scratch the walls of the 25 – mL beaker with a glass
rod to induce crystallization. When the crystals appear, transfer the beaker into the ice – water
bath to complete the crystallization.
4. Add 5mL of cold distilled water to the crystals. Stir thoroughly.
5. Set up a vacuum filtration using a Buchner funnel and a 250 – mL filter flask connected to a
filter trap and an aspirator. Wet the filter paper with the water and aspirate.
6. Collect the product crystals by vacuum filtration. Pour the crystals into the Buchner funnel.
Rinse the beaker with 1 mL of cold water and add the rinse to the Buchner funnel.
7. Rinse the crystals with an additional 1mL of cold water.
8. Transfer the crystals to a watch glass. Allow the crystals to dry.
Product characterization
1. Label four test tubes 1 – 4. Put 0.5 mL of distilled water in each tube.
2. Add a few milligrams of salicylic acid to tube 1. Add a few milligrams of aspirin to tube 2. Add a
few milligrams of your product to tube 3. Use tube 4 as a control.
3. Shake tubes 1 – 3 to dissolve the crystals. Add one drop of 1% FeCl 3 to each of the four tubes.
Record the results.
Course: CHEM 005 Experiment No.: 8
Group No.: 2 Section: CH41FB1
Group Members: Date Performed: March 2, 2018
ISLA, Stephen Nikoe P. Date Submitted: March 12, 2018
MARTI, Benedick Jayson P. Instructor: Engr. Juanita Apostol
MONSALUD, Lea E.
MAWILI, Mia. Beatrice V.
6. Data and Results:
Mass of Salicylic Acid Used: 3.02 g
Mass of Acetylsalicylic Acid Produced: 2.67 g
Theoretical Yield: 3.94 g
Percent Yield: 67.77%
7. Questions:
1. Describe the results of the reaction you conducted with 1% FeCl3.
The first reaction we examined is the effect of adding one drop of 1% FeCl3 to a test tube 1
which contains a few milligrams of salicylic acid. The color of the mixture turned to purple and few icy like
crystals emerged on the surface of the mixture.
The second reaction we examined is the effect of adding one drop of 1% FeCl3 to a test tube 2
which contains a few milligrams of aspirin we bought from a local drug store. The color of the mixture
remained the same as the yellowish color of the aspirin and some bubble formed on the surface of the
mixture.
The third reaction we examined is the effect of adding one drop of 1% FeCl3 to a test tube 3 which
contains a few milligrams of our product. The color of the mixture turned to yellowish color and crystals
emerged on the surface of the mixture.
The fourth and last reaction we examined is the effect of adding one drop of 1% FeCl3 to a test
tube 4 which contains a few milligrams of distilled water as control. The color of the mixture slightly
resembled the color of the aspirin. No crystals or other significant formations were observed.

2. What do the results indicate about your product? Briefly Explain.

With the result of adding of 1% FeCl3 solution on our product, we conclude that it is an aspirin.

8. Documentation:
 SET UP OF EQUIPMENT ICE – WATER BATH

VACUUMING OF PRODUCTS ASPIRIN TEST

9. Conclusions:
We therefore conclude that in this experiment, we can synthesize aspirin from salicylic acid with the
acetyl anhydride. And also, we learned that crystallization is important in producing aspirin and we can
initiate crystallization with our will through scratching the wall of the glassware that contains aspirin solution.