Synthesis of Aspirin and Wintegreen Spring 2006
Synthesis of Aspirin and Wintegreen Spring 2006
Synthesis of Aspirin and Wintegreen Spring 2006
Cautions
Acetic Anhydride – corrosive and a lachrymator – all transfers should be done in the vented fume hood
Ethanol – flammable and highly toxic
Methanol – flammable and highly toxic
Salicylic Acid – toxic and irritant
Sulfuric Acid – highly toxic, corrosive, and an oxidant
Phosphoric Acid – highly toxic, corrosive, and an oxidant
Purpose
To synthesize acetylsalicylic acid (aspirin) and methyl salicylate (oil of wintergreen).
Introduction H O
that these compounds act within the human body to thwart or inhibit the production of prostaglandins, which are
used in the perception of pain.
Methyl salicylate is the active ingredient in Oil of Wintergreen. It has a very distinct odor and the flavor of
spearmint. It is used commonly in ointments for the relief of muscle pain and cramping because it can penetrate
the skin and give relief to muscles. It also has found a use as a flavoring agent in other compounds.
Procedure
Synthesis of Aspirin
1. Heat, using a hot water bath located in the hood, 250 mL of water in a 400 or 600 mL beaker to 70-
85OC. Continue on to steps 2-6 while heating.
2. Place 75 mL of DI water into a small Erlenmeyer flask; place the flask into a large beaker of ice water.
Continue on to steps 3-6 while the water is being chilled.
3. Weigh 2.5 ± 0.25 grams of salicylic acid into a 125 mL Erlenmeyer
flask. Record the weight of the salicylic acid.
4. Carefully add 5.0 mL of acetic anhydride to the flask along with 7
drops of phosphoric acid. Swirl the flask carefully to ensure mixing
of the reagents.
5. Heat the water bath to between 70-85OC. Place the flask in the hot
water and secure the flask to the ring stand using a utility clamp.
Heat the solution for 20 minutes stirring occasionally using a glass
stirring rod.
6. After heating remove the flask carefully and immediately add 2.0 mL
of DI water to the flask. The addition of the water will react with any
excess acetic anhydride to convert it to acetic acid. Avoid breathing
in the acetic acid vapors.
7. Add 30.0 mL of cold (chilled in an ice bath) DI water to the flask.
Then place the flask in an ice bath to complete the crystallization
process for at least 10 minutes.
8. Collect the crystals by vacuum filtration using a Büchner funnel. Note: use thick walled tubing to the
vacuum line, do not fold the filter paper, and wet the paper with a small amount of DI water under
vacuum before adding your sample. Wash your crystals with a small amount of cold DI water. Let
the crystals dry on the filter paper with the vacuum for 5 minutes.
9. Dry the crystals by spreading them on a piece of filter paper or paper
towel and patting them gently dry with another piece of filter paper.
10. Weigh and record your actual yield of aspirin.
11. Calculate the theoretical yield and percent yield of aspirin.
Data Sheet
Show all calculations on another sheet of paper and attach to the lab.
Name: ____________________________________________
Synthesis of Aspirin
Moles of Acetic
Anhydride Percentage Yield
(Density = 1.080 g/ml)
Observations
Observations
Color
Smell
Other
Characteristics
Post-Lab Questions
Name: ______________________________________
1. Aspirin may loose its medicinal properties if allowed to reside on a shelf in a moist atmosphere. This
decomposition process will develop an acetic acid smell (i.e. vinegar), write the balanced decomposition reaction.
2. A student gets a yield of 88% from his salicylic acid. How many grams of salicylic acid will the student need to
produce 123 g of aspirin?
3. Based on your yield that you obtained in your experiment, how much salicylic acid would you need as starting
material to produce 25.00 g of aspirin?
4. What steps could have been taken to improve your percent yield of aspirin?
Pre-lab Assignment
Name: _________________________________
1. List the hazards and dangers present in this lab and the precautions that should be followed.
a. Analgesic
b. Antipyretic
3. A student begins with 2.22 g of salicylic acid (MW=138 g/mol) and 4.04 mL of acetic anhydride (MW=102 g/mol
density=1.081 g/mL) in the preparation of aspirin. Show your calculations in the space below.
d. Calculate the theoretical yield for the reaction in moles and in grams of aspirin.