Aspirin (Experiment #1)

William Butler and Fernando Marquez

I. Introduction
Acetylsalicyclic acid, or Aspirin, belongs to a group of medications called anaglesics.
These medications can be used to reduce fever, swelling, and relieve pain. Felix Hoffman
(1893) is created for discovering the synthesis of aspirin while working for the Bayer, the
German chemical company. Today, 80 million aspirin tablets are used daily and is found in
over 100 nonprescription drugs.
1

The goal of this experiment was to synthesize Aspirin by using H
2
SO
4
(sulfuric acid) in
an acid catalyzed acetylation reaction. Essentially, sulfuric acid speeds up the rate of the
reaction without creating unwanted products. This allows salicyclic acid and acetic anhydride
to create acetyl salicyclic acid and acetic acid, as seen in figure 1:


Figure 1: Synthesis of Aspirin via Acid Catalyzed Acetylation Reaction
2

To help purify this reaction, the crude product can be recrystallized. This process
involves re-dissolving the crude product. When placed in a second solvent, the molecules can
interact more selectively and can be refiltered.

The purity of this process can be tested through two different methods; the Ferric
Chloride Test and by measuring the melting point of the final product. The phenol test serves
as a quality control for the amount of phenol (found in the starting material) that results in the
product. The ferric chloride test for phenols is assessed qualitatively. Once the test is
conducted, a color change from orange to purple is a positive test for the phenol group. If this
is the case, then the product is not pure and the crude product must be recrystallized, as
described above.

The second test for purity involves a Mel-Temp Apparatus which is a machine that can
be used to measure the melting point of a solid. The ideal melting point of pure acetyl
salicyclic acid is 136 C
o
. By using the Mel-Temp Apparatus, the actual melting point can be
compared to the ideal melting point. A compound is considered pure when it is within 2
o
C of
the pure substance. Impurities with the crystal lattice will disrupt this trend and cause a
melting point that is lower than the idea.

II. Results and Discussion
Limiting Reagent: Salicyclic Acid (2g)
Excess Reagent: Acetic Anhydride (5 ml)
Salicyclic Acid: 2 grams (1 mol/138.12 g) = 0.014 moles
Acetic Anhydride: 5 ml (1.08 g/1 ml) = 5.4 grams (1 mole/102.09 grams) = 0.05 moles
Because .014 mol < 0.05 mol, salicyclic acid is present in lesser amounts and is the limiting
reagent.
Theoretical Yield of Acetyl Salicyclic Acid:
0.014 mol C
7
H
6
O
3
(1 mol C
9
H
8
O
4
/1 mol C
7
H
6
O
3
) = 0.014 mol C
9
H
8
O
4
0.014 mol C
9
H
8
O
4
= (180.16 g C
9
H
8
O
4
/ 1 mol C
9
H
8
O
4
) = 2.52 g Salicyclic Acid
Crude Product Actual Yield:
Percent yield = actual/theoretical x 100%
= 2.126 g/2.612 g = 81.38%

No Recrystallization necessary.
Melting Point of Pure Acetyl Salicyclic Acid: 136
o
C
Melting Point of Product: 115
o
C
Results from Ferric Chloride Test
Color After the Addition of Ferric Chloride
Salicyclic Acid Purple
Crude Product Orange/Clear
Recrustalized Product N/A

Although the crude product yield was only moderately high, the phenol test did not
require recrystallization. This provided evidence that our product was mostly pure but there may
have been functional errors in measurements which deviated from the ideal yield. The Ferric
Chloride test for Phenols did not render a purple hue which would have been indicative of a
phenol group which was not desired. The phenol test was mostly clear which means that the
phenols were only found in the reactants, as expected.
The expected melting point was 136
o
C while the experimental melting point was 115
o
C.
To be considered pure, the melting point would have to be within 2
0
C of the ideal melting
point. This would mean that our experimental melting point would have to be 134
o
C or higher
which it was not. This suggests impurity with the sample. These impurities are often attributed to
weak binding between the molecules. It is likely that the sample was wet which would account
for a relatively pure crude product with a lower melting point.
As a result of the ferric chloride test it can be determined that our product was relatively
pure. This is because the product did not possess purple character. Ambiguity can be found in the
relatively moderate yield and the low melting point. These results suggest that both random and
systematic errors were involved. A lower than expected yield could be due to measuring errors
while the lower melting point could be rationalized systematically as the Mel-Temp requires a
dry sample. Still, this experiment is considered a success given the purity of our product and the
amount of information learned.
III. Experimental
2.0 grams of salicyclic acid, 5 ml of acetic anhydride, and 5 drops of sulfuric acid were
added to a 125 ml Erlenmeyer flask and swirled until dissolved. The solution was then heated
with a water bath and kept at 50
o
C for 10 minutes. The product was then cooled to room
temperature for crystallization. The crystals were then collected by vacuum filtration with 50 ml
H
2
O. The crystals were rinsed with water and vacuum dried. The crude product was collected
and weighed. This was used to calculate the percent yield. The ferric chloride test was then
performed. This test was used to determine the presence of unwanted phenols in the crude
product. A color change from orange to purple is indicative of phenols. 10 drops of FeCl
3
was
added to saliclycic acid which served as a control and the crude product. The salicyclic acid was
purple as expected and the product was orange. The data for this experiment can be found above
in the Results and Discussion.
IV. References
1) Kluger, E. Introduction to Organic Lab Techniques. CHM 2211L, 2011. Print.
2) University of California, Davis.
http://chemwiki.ucdavis.edu/@api/deki/files/2782/image063.png?revision=1 (access
May 27, 2014).