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

To synthesize Acetylsalicylic acid
from the reaction of Salicylic acid with
Acetic Anhydride and 85% phosphoric Acid
and also, to determine the obtained
product’s melting point and its solubility in
water and toluene.
Introduction
Acetylsalicylic Acid, also known by
trade name Aspirin, is an acetyl derivative of
salicylic acid that is a white, crystalline,
weakly acidic substance, with melting point
137°C. It is useful in the relief of headache
and muscle and joint aches. Aspirin is also
effective in reducing fever, inflammation,
and swelling and thus has been used for
treatment of rheumatoid arthritis, rheumatic
acid-base imbalance and respiratory
disturbances and can be fatal, especially in
children. Acetaminophen (known by trade
name Tylenol), which does not cause gastric
irritation but does lower fever and relieve
pain, is often substituted for Aspirin. The
synthesis of aspirin is classified as an
esterification reaction. Salicylic acid is treated
with acetic anhydride, an acid derivative,
causing a chemical reaction that turns salicylic
acid's hydroxyl group into an ester group (R-OH
→ R-OCOCH3). This process yields aspirin and
acetic acid, which is considered a byproduct of
this reaction. Small amounts of sulfuric acid
(and occasionally phosphoric acid) are almost
always used as a catalyst. This method is
commonly employed in undergraduate teaching
labs.
Methodology
The synthesis of Acetylsalicylic acid
was done using a macroscale technique.
Salicylic Acid (1g), boiling chip, 85%
phosphoric acid (1 drop), and Acetic
Anhydride (2mL) were mixed in a test 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
added and the mixture was let to cool at
room temperature. The crystals were formed
and the tube was put into an ice bath. The
crystals were filtered, dried and weighed.
Some sample of the crystals was put in a
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
ratio of 1:9 and the second was 1:1
respectively. Some sample of the product
was put in two test tubes, one with water and
the other with toluene to determine its
solubility.
Determine the melting point of the
crystals using oil bath or John Fisher
melting point apparatus. Perform thin
layer chromatography with three
spots, reactant, co-spot and product.
Test the solubility of the product in
water and toluene. Observe if it
dissolves completely.
Figure 1: Synthesis of Acetylsalicylic Acid
Add 1.00 g of salicylic acid, a boiling
chip, and one small drop of 85%
phosphoric acid followed by 2.0 mL of
acetic anhydride (the acetic anhydride
serves to wash the reactants to the
bottom of the tube).
Mix the reactants thoroughly, the heat
the reaction tube on a steam bath or in a
beaker of 90̊C water for 5 minutes. Add
2.0 ml of water to the reaction mixture to
decompose the excess acetic anhydride.
(caution: exothermic reaction).
Add an additional 1.0 ml of water and
allow the reaction to cool slowly at
room temperature. (if crystallization of
the product does not occur during the
cooling process, scratch the inside of the
tube with glass stirring rod. Cool the
tube in an ice bath.
Remove the solvent using Pasteur
pipette. Add 1-2 ml of iced water
and filter the crystals between the
sheet of filter paper and squeeze the
crystals between the filter to absorb
excess water. Allow the product to
air dry thoroughly before
determining the weight and calculate
the percent yield.
Results and Discussion
The product obtained is a white
crystalline solid that gave a percentage yield
of 58.52%. The melting point range
determined was 136̊C-140̊C which suggests
that the product obtained is impure. Because
the difference is greater than 1̊C-2̊C and the
melting point range obtained is lower than
the true value of the melting point range of
Acetylsalicylic Acid which is 138̊C-140̊C.
The results obtained from Thin Layer
Chromatography can be seen in Table 1
which suggests that the product obtained is
still a mixture of the starting material
the synthesized product because their Rf
values are near to each other. This result is
visible with both of the solvents that were
used.
The product obtained is slightly soluble in
water and soluble in toluene. This is because
of the polarity of the product. Since
Acetylsalicylic has only one OH bond it is
only slightly soluble in water. It is soluble in
toluene because of its many non-polar sites
applying the rule of like dissolves like.
Conclusion
I therefore conclude that the product
obtained is impure. It may be a mixture of
Acetylsalicylic Acid and unreacted Salicylic
Acid. My conclusion is due to the results of
the experiment, the melting point range
yielded and the Thin Layer Chromatography
results.
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)