SYNTHESIS OF ASPIRIN

By/Mohamed Ali Mohamed

ID/143445
Abstract
The experiment aim is to synthesis aspirin via esterification. Aspirin is known as acetylsalicylic
acid as a scientific name and have a molecular formula C 9H8O4, by using the reaction between
salicylic acid and acetic anhydride with a presence of H 2SO4 concentrated. The products of this
reaction are aspirin and acetic acid, by separating acetic acid, we will get a pure product of
aspirin during recrystallization with a presence of hot ethanol.
Contents
Abstract.......................................................................................................................................................1
Introduction.................................................................................................................................................3
Procedure....................................................................................................................................................5
Discussion....................................................................................................................................................6
Results.........................................................................................................................................................8
References...................................................................................................................................................9
Introduction
Aspirin, also known by scientific name acetylsalicylic acid which have this
molecular formula C9H8O4. At present, salicylic acid is administered in the
form of aspirin which is less irritating to the Stomach of salicylic acid. To
prepare aspirin, react with salicylic acid with excess acetic acid Anhydride.
A small amount of strong acid is used as a catalyst that accelerates the
reaction. In this Phosphoric acid will be used as a catalyst. The excess acetic
acid will be put down with add the water [ CITATION Tay11 \l 1033 ]. The aspirin product is not
soluble in water so the aspirin product Hurries when adding water. The synthesis reaction of
Aspirin is given below: -

The acetic Anhydride will act as both a reactant and a solvent, a technique common in synthesis.
When all salicylic acid is converted to aspirin, water will be added. This transform the acetic
anhydride of acetic acid [ CITATION Eld07 \l 1033 ]. The reaction appears below. Reaction is
example of hydrolysis, division (decomposition) material with water as shown below: -
Aspirin works by suppressing the synthesis of prostaglandin and thrombocytes in Human body.
Prostaglandins function as local hormones produced in the body which helps in Transmission of
pain signals, regulation of hypothermia, inflammation. Thromboxane are involved in the
aggregation of platelets forming blood clots. Do it before the irreversible disruption of
prostaglandin endoperoxide synthase (PTS), also known as Cyclooxygenase 2, an enzyme that is
required in the synthesis of prostaglandin and thromboxane. Aspirin acts as an acetylating agent
where the acetyl covalent group is bonded with serine Residues in an active site of prostaglandin
endoperoxide Sensate Enzyme [ CITATION Jan87 \l 1033 ].
Procedure
1- By using a 50-mL flask. Put about two grams of salicylic acid in the flask and weigh
again. In the fume hood, then we will transfer 5.0 mL of acetic anhydride from a burette
into the flask. Add three drops of catalyst to the flask.
2- Put the flask in a beaker of tap water over a burner flame. Then dissolve the salicylic
acid. Then we must be heating the water to boiling, and turn off the flame. Keep the flask
in the hot water bath for ten more minutes.
3- While the flask is in the water bath, we will add 2 mL of distilled water to the flask to
decompose any acetic anhydride which maybe excess.
4- After five minutes, we will remove the flask from the water bath and we will add twenty
mL of distilled water. Let the sample cool to normal temperature of the room. As the
sample cools, crystals will appear. Cool the sample by putting the reaction flask in a cold
bath.
5- Measure weight of filter paper and watch glass.
6- Set up a Büchner funnel on a vacuum flask connected to a water aspirator. Switch on the
aspirator and transfer the aspirin in the funnel.
7- It is safe to discard of the filtrate down the sink with water.
Discussion
1- Phenols are not acidic than carboxylic acids, but they are more acidic than alcohols, and
they are more acidic than water. Unlike simple alcohols because it has a partial positive
charge on the oxygen atom due to resonance into the benzene ring.

oxygen is
called electronegative atom, the electrons in the oxygen and hydrogen bond orbital will
attack the oxygen atom, giving us the positive hydrogen. Loss of a hydrogen ion to a base
creates a
phenoxide
ion that is
resonance
stabilized
[ CITATION
Ela09 \l 1033 ].

the pKa values of phenols, alcohols and carboxylic acids which are shown that the carboxylic
acids have the smallest value of pKa comparing to alcohols and phenols this makes the
carboxylic acids are the most acidic components.

2- The reaction: -
3- The mechanism: -
4- The main different of esterification of alcohol and of phenols that alcohols can reacted

with carboxylic acids, but phenols can’t have reacted with carboxylic acids.
5- To complete esterification reaction, we must add strong acidic solution like phosphoric
acid. Alcohols can react with this acid because alcohols are proton acceptor unlikely the
phenols which can’t react with this acid because phenols can’t accept any protons.
Results
1- Steps to get pure product: -

By using 5 mg of crude acetylsalicylic into TLC analysis. The aspirin sample will be added
to a 125-ml flask. About 60 mL of hot ethanol/water solvent will be added slowly to the
aspirin sample in a water bath. Then the crystals will be dissolved, then we must be cooling
the flask to have the same temperature of the room for ten minutes, it will be fully
crystallizing. Then, the crystals were placed into a vacuum filter where they Were
subsequently rinsed with two 3 mL portions of cold deionized water and one 2 mL port of
cold ethanol.

2- Two different techniques: -

chromatographic or spectrophotometric methods and titration analysis.
Titration analysis: -
- Weight accuracy must be between 0.1 and 0.15 g of the product of aspirin into a flask.
-Then by adding ethanol and swirl to dissolve. By adding two drops of phenolphthalein
indicator to the flask.
-by using 0.1 M of NaOH.
Thin layer chromatography: -
chromatography in which a liquid sample moves by capillarity into a solid adsorbent
medium like alumina or silica gel which is arranged as a thin layer on a glass plate.
References
Aldred, E. M. (2009). Pharmacology. UK.

Eldredge, P. (2007). Chemistry. new york : pearson education.

Francis, T. &. (2011, may 23). aspirin. Retrieved from College. Work. Life afterwards.:
http://theuplbcollegestudent.blogspot.com.eg/2011/05/full-report-synthesis-of-aspirin.html

McTavish, J. R. (1987). aspirin. Aspirin in Germany: The Pharmaceutical Industry and the Pharmaceutical
Profession, 103-115.