Aspirin Synthesis Post Lab

Acetylsalicylic Acid Synthesis
POLYTECHNIC UNIVERSITY OF THE PHILS.

Gregorio, Marielle P.1
1
Department of Physical Sciences, College of Science, Sta. Mesa, Manila.
Date Performed: March 2, 2012

Date Submitted: March 8, 2013
Abstract
This experiment was conducted to synthesize Acetylsalicylic Acid (Aspirin) from the reaction of
Salicylic Acid with Acetic Anhydride and 85% Phosphoric acid using a macroscale technique.
The product obtained gave a percent yield of 58.52%. The crystals formed were dried and was
subjected to thin layer chromatography and melting point determination which yielded a melting
point range of 138̊C-140̊C. This suggests that the product obtained is impure.
Key words: thin layer chromatography, macroscale technique
Objectives fever, and mild infection. Large doses cause

acid-base imbalance and respiratory
To synthesize Acetylsalicylic acid disturbances and can be fatal, especially in
from the reaction of Salicylic acid with
children. Acetaminophen (known by trade
Acetic Anhydride and 85% phosphoric Acid
and also, to determine the obtained name Tylenol), which does not cause gastric
product’s melting point and its solubility in irritation but does lower fever and relieve
water and toluene. pain, is often substituted for Aspirin. The
synthesis of aspirin is classified as an
Introduction esterification reaction. Salicylic acid is treated
with acetic anhydride, an acid derivative,
Acetylsalicylic Acid, also known by causing a chemical reaction that turns salicylic
trade name Aspirin, is an acetyl derivative of acid's hydroxyl group into an ester group (R-OH
salicylic acid that is a white, crystalline, → R-OCOCH3). This process yields aspirin and
weakly acidic substance, with melting point acetic acid, which is considered a byproduct of
137°C. It is useful in the relief of headache this reaction. Small amounts of sulfuric acid
and muscle and joint aches. Aspirin is also (and occasionally phosphoric acid) are almost
always used as a catalyst. This method is
effective in reducing fever, inflammation,
commonly employed in undergraduate teaching
and swelling and thus has been used for
labs.
treatment of rheumatoid arthritis, rheumatic
Methodology
Add 1.00 g of salicylic acid, a boiling
chip, and one small drop of 85%
The synthesis of Acetylsalicylic acid
was done using a macroscale technique. phosphoric acid followed by 2.0 mL of
Salicylic Acid (1g), boiling chip, 85% acetic anhydride (the acetic anhydride
phosphoric acid (1 drop), and Acetic serves to wash the reactants to the
Anhydride (2mL) were mixed in a test tube. bottom of the tube).
The solution was stirred and heated in a
water bath at 90̊C for 5 minutes. Water
(2mL) was added that causes an exothermic
reaction and another 1mL of water was Mix the reactants thoroughly, the heat
added and the mixture was let to cool at the reaction tube on a steam bath or in a
room temperature. The crystals were formed beaker of 90̊C water for 5 minutes. Add
and the tube was put into an ice bath. The 2.0 ml of water to the reaction mixture to
crystals were filtered, dried and weighed. decompose the excess acetic anhydride.
Some sample of the crystals was put in a (caution: exothermic reaction).
capillary tube to determine the melting point
of the obtained product in an oil bath. Thin
layer Chromatography was performed and
the solvents used were Ethyl Acetate and
DCM. The first solvent we used was in a Add an additional 1.0 ml of water and
ratio of 1:9 and the second was 1:1 allow the reaction to cool slowly at
respectively. Some sample of the product room temperature. (if crystallization of
was put in two test tubes, one with water and the product does not occur during the
the other with toluene to determine its cooling process, scratch the inside of the
solubility. tube with glass stirring rod. Cool the
tube in an ice bath.
Determine the melting point of the Remove the solvent using Pasteur
crystals using oil bath or John Fisher pipette. Add 1-2 ml of iced water
melting point apparatus. Perform thin and filter the crystals between the
layer chromatography with three sheet of filter paper and squeeze the
spots, reactant, co-spot and product. crystals between the filter to absorb
Test the solubility of the product in excess water. Allow the product to
water and toluene. Observe if it air dry thoroughly before
dissolves completely. determining the weight and calculate
the percent yield.
Figure 1: Synthesis of Acetylsalicylic Acid

Results and Discussion The product obtained is slightly soluble in
water and soluble in toluene. This is because
The product obtained is a white of the polarity of the product. Since
crystalline solid that gave a percentage yield Acetylsalicylic has only one OH bond it is
of 58.52%. The melting point range only slightly soluble in water. It is soluble in
determined was 136̊C-140̊C which suggests toluene because of its many non-polar sites
that the product obtained is impure. Because applying the rule of like dissolves like.
the difference is greater than 1̊C-2̊C and the
melting point range obtained is lower than Conclusion
the true value of the melting point range of
Acetylsalicylic Acid which is 138̊C-140̊C. I therefore conclude that the product
The results obtained from Thin Layer obtained is impure. It may be a mixture of
Chromatography can be seen in Table 1 Acetylsalicylic Acid and unreacted Salicylic
which suggests that the product obtained is Acid. My conclusion is due to the results of
still a mixture of the starting material the experiment, the melting point range
the synthesized product because their Rf yielded and the Thin Layer Chromatography
values are near to each other. This result is results.
visible with both of the solvents that were
used. References:
Pavia, D.L., Lampan, G.L., Kriz, G.S.,

Engel, R.G., Microscale and Macroscale
Techniques in the Organic Laboratory,
2002, 1st
Williamson, K.L., Masters, K.M.

Macroscale and Microscale Organic
Experiments, 2007, 6th
Retrieved from World Wide Web March 07,

2013
http://www.chemicalland21.com/arokorhi/lif
escience/phar/acetylsalicylic%20acid.htm
Figure 2: TLC plate of solvent ration 1:9
Table 1: Rf values
Solvent Ratio Reactant Co- Product
(Rf spot (Rf
value) (Rf value)
value)
1:9 (0.5mL 0.64 0.59 0.55
EA,
4.5mLDCM)
1:1 (2.5mL 0.13 0.13 0.9
EA,2.5mL
DCM)

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Acetylsalicylic Acid Synthesis

POLYTECHNIC UNIVERSITY OF THE PHILS.

Date Performed: March 2, 2012

Key words: thin layer chromatography, macroscale technique

Objectives fever, and mild infection. Large doses cause

Figure 1: Synthesis of Acetylsalicylic Acid

Pavia, D.L., Lampan, G.L., Kriz, G.S.,

Williamson, K.L., Masters, K.M.

Retrieved from World Wide Web March 07,

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