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Synthesis of Aspirin and Wintergreen

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

Organic chemistry is a vital H O


H C C
O O C C OH O
part in the majority of the chemical C C
H
C C OH H+ C C +
C C C
industry whether it is in plastics, + H3C O CH3 H C O H3C OH
C C
H C OH
petroleum, polymers, H
O
C
CH3
H
pharmaceuticals, and/or health and
Salicylic Acid Acetylsalicylic Acid Acetic Acid
Acetic Anhydride
beauty aids. Many everyday H O H O

products are primarily comprised H C C H H C C CH3


C C OH C C O H O
of organic molecules. During this H C OH H+
C C + C C
H

experiment, you will synthesize H C OH H H C OH +

two organic esters, acetylsalicylic H H


Salicylic Acid Methanol Methyl Salicylate Water
acid and methyl salicylate.
An ester is a type of organic compound that contains carbon atoms doubly-bonded to an oxygen and
singly-bonded to other carbon or oxygen atoms. Typically, volatile esters have pleasant odors and are
responsible for the inviting aromas and fragrances of fruits and flowers. The fragrant aroma of esters has been
exploited by cosmetic industry in the production of cosmetics and perfumes. The food and pharmaceutical
industry also use the properties to their advantage in the form of flavoring agents in solid and liquid products.
Aspirin is the most widely used medical compound throughout the world. The chemical name for aspirin
is acetylsalicylic acid and the organic compound is a white solid that has a very low solubility in water (0.25 g in
100 ml of water). An aspirin tablet will usually contain 325 mg of acetylsalicylic acid held together with an inert
binder such as starch. Aspirin is derived from salicylic acid which occurs naturally in the bark of willow trees.
Both of these compounds are important due to their O
OH
analgesic (pain reliever) and antipyretic (fever O C CH3
HO CH
reducer) properties. Aspirin is less acidic than C
OH
salicylic acid which helps in the reducing the
number of stomach, mouth, and mucus membrane O
HN CH3
irritations. Therefore, it is used instead of salicylic C
C
O CH3
acid. However, some people find that aspirin is still O
H2C CH3
CH
too acidic and may opt for some of the less acidic
CH3
alternatives such as Tylenol or Advil. It is believed Aspirin Tylenol Advil
Acetylsalicylic Acid Acetaminophen Ibuprofen

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Synthesis of Aspirin and Wintergreen

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.

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Synthesis of Aspirin and Wintergreen

Synthesis of Oil of Wintergreen


1. Weigh 0.25 grams of salicylic acid into a 10-15 cm test tube. This weight does not need to be
recorded.
2. Add 2.0 mL of methanol to the test tube and swirl until the solid dissolves.
3. Slowly add 10 drops of sulfuric acid.
4. Place the test tube in a hot water bath and secure by using a utility clamp and heat for 15 minutes.
5. Cool the test tube in running water.
6. Smell the contents and record your observations.
Disposal
Place all waste and compounds in the appropriate labeled waste bottles in the laboratory.
Clean-Up
Wash all glassware with soap then rinse 3 times with tap water, and once with deionized water.

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Synthesis of Aspirin and Wintergreen

Data Sheet
Show all calculations on another sheet of paper and attach to the lab.

Name: ____________________________________________

Synthesis of Aspirin

DATA UNITS DATA UNITS

Mass of Salicylic Acid Mass of Aspirin Product

Moles of Salicylic Acid Moles of Aspirin Product

Volume of Acetic Theoretical Yield


Anhydride

Moles of Acetic
Anhydride Percentage Yield
(Density = 1.080 g/ml)

Observations

Synthesis of the Oil of Wintergreen

Observations

Color

Smell

Other
Characteristics

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Synthesis of Aspirin and Wintergreen

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?

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Synthesis of Aspirin and Wintergreen

Pre-lab Assignment

Name: _________________________________

1. List the hazards and dangers present in this lab and the precautions that should be followed.

2. Briefly define the following terms:

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.

a. How many moles of salicylic acid were used? ____________________

b. How many moles of acetic anhydride were used? ____________________

c. Which compound is the limiting reagent in the preparation of aspirin? ____________________

d. Calculate the theoretical yield for the reaction in moles and in grams of aspirin.

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