Preparation of Aspirin

Objectives:
1. To synthesize aspirin using salicylic acid and acetic anhydride as substrates
2. To calculate the percent yield obtained based from computed theoretical and actual yields
Schematic Diagram
A. Synthesis of Aspirin Sample
1.9- 2.2 g Salicylic Acid
Add 5.0- 5.5 ml of Acetic Anhydride
No visible reaction formed
Add 5 drops of 85% H3PO4
Orange-Brown solution color formed
Heat at 75C for 15 minutes
Reaction Completed
Add 2 ml water
Acetic acid vapor produced
Add 18-20 ml water. Cool.
Crystals of aspirin appears
Place in ice bath
Crystallization hastens
Filter, dry and weigh
Aspirin weight recorded

Results/Discussion
The table presented below denotes the pertinent data needed for the determination of the
percentage yield of the synthesized aspirin sample.
Table 1. Data for the determination of the percent yield in synthesized aspirin sample

Subject
Mass of Erlenmeyer Flask
Mass of flask and salicylic acid
Mass of salicylic acid
Mass of watch glass
Mass of watch glass and aspirin
Mass of aspirin (actual yield)
Mass of aspirin (theoretical yield)
Percentage Yield (%)

Amount (g)
91.3653
93.3454
1.9801
33.2348
34.4261
0.4571
2.5831
17.70

The determination of the percentage yield of the ASA sample by using the formula
actual yield
[ Eq.1 ] Percentage Yield=
100
theoretical yield
The theoretical yield of the aspirin sample produced can be determined by using the formula
mol ASA
[ Eq.2 ] Theoretical yield=sample gsalicylic acid MW salicylic acid
MW ASA
mol salicylic
where ASA stands for acetylsalicylic acid (Aspirin). Based from Table 1, there is 1.9801 g of
salicylic acid used. Applying [ Eq.2 ] , we get
Theoretical yield=1.9801 g salicylic acid

mol
mol ASA
180.157 g
salicylic acid

ASA
138.1
mol salicylic acid
mol

2.5831 g ASA

Meanwhile, the actual yield produced can be determined by the formula

[ Eq.3 ] Actual yield =wt . of sample containerweight of container
Looking back again in Table 1, it could be known that the aspirin sample is placed in a
watch glass (used as a container). Subtracting the values, we get
Actual yield=wt . of sample watch glassweight of watch glass
34.4261 g33.2348 g=0.4571 g
Since the two variables are already known, hence,
actual yield
Percentage Yield=
100
theoretical yield

0.4571 g
100=17.70 ASA
2.5831 g

Based from the result obtained, it could be easily determined that the percentage yield
was comparatively lower compared to the expected yield. This huge error may have been due to
the crystallization process, where not all ASA were retrieved during the crystallization has been
carried out, or simply due to the loss of sample due to mishandling in storage. In addition, the

synthesized aspirin crystals were colored peach-like instead to that of expected white. The
rationale can be pointed out to the excess H3PO4 added that gave of a brown solution color.
Conclusion
The synthesized aspirin sample was prepared using salicylic acid and acetic anhydride.
Results shown that there is a percentage yield of 17.70% ASA content in the sample, which
implies that the prepared aspirin did not reach the expected amount that will be produced. It can
be reasoned out to the immature crystallization or simply due to the improper handling and
storage of the sample produced.

Reaction Mechanisms
The synthesis of acetylsalicylic acid (aspirin) is carried out through this manner:

This reaction covers a series of steps, which can be enumerated as follows:

1) In the first reaction, a proton (H +) from the acid attacks the oxygen in acetic anhydride. This
causes two electrons in the double bond to delocalize across the two oxygen atoms on the acetic
anhydride.

2) SA now acts as a nucleophile, with a free pair of electrons on the oxygen of the hydroxyl
group attacking the carbon of the acetic anhydride. The delocalized electrons rearrange, creating
a temporary bond between the two reactants. Due to the extra proton attached to the oxygen
atom, the oxygen is positively charged.

3) In the third reaction, the proton from the hydroxyl group of the phenol attacks the oxygen in
the original
OH portion of
the
acetic
anhydride, fo
rming
a
positively
charged oxygen
atom.

4) In reaction 4, due to the now positive charge on the oxygen, electrons bonding the C and O +
atoms are donated to the oxygen atom. This breaks the bond between the two and forms acetic
acid, a by-product of the synthesis of ASA. At the same time, electrons between the OH and C
rearrange to reform a double bond between C=OH. This causes the OH group to become
positively
charged
due
to
loss
of
negative
electrons.

5) Finally, the 5th stage illustrates how the positively charged -OH group loses a proton to reform
the H3PO4 catalyst, leaving the ester, ASA, behind.