Laboratory Skills

Jelisaveta Mirkovic 12/04/14

Introduction
This experiments purpose was to review lab techniques such as recrystallisation and filtration by
synthesising and purifying acetylsalicylic acid (aspirin). The synthesis is an esterification
mechanism, with a by-product of acetic acid.
Experimental
In the fumehood, 1 drop of concentrated sulfuric acid was added to a solution of salicylic acid (1.0
g, 7 millimoles) in acetic anhydride (1 mL, 0.01 moles). This solution was warmed for 15 minutes
and then cooled on ice to form crystals. The solid was collected by vacuum filtration (2.33 g), and
then recrystallised using boiling water. The product was acetylsalicylic acid. Yield 0.5 g, (40%).
Melting point range: 124 134 C
Results and Discussion
Literature value for melting point: 135 C
[1]

My lower melting point and also the size of the range indicates that the compound I made had
impurities (such as unevaporated water). My low yield (40%) could have been improved by better
transference of the solid after filtration, and also by making sure to use only the minimum volume
of boiling water during recrystallisation.
a)
b)

1H NMR Spectra for a) salicylic acid, and b) aspirin (from Blackboard)

Questions
There are 5 different Hydrogen environments in the 1H NMR spectrum for salicylic acid. From the
highest chemical shift (~10.5 ppm), the number of signals at each peak is 1, 2, 3, 2, 3. Aspirin also
has 5 hydrogen environments, but they are much more spread out. The number of signals at each
peak (starting at the peak with the highest chemical shift ~8.1) is 2, 3, 3, 2, 1.
Conclusion
Acetylsalicylic acid (aspirin) was synthesised from acetic anhydride and salicylic acid, the yield
was quite low and the product was impure (due to water), as evidenced by the large melting point
range.
References
[1] O'Neil, M.J., (Ed.). (2006). The Merck Index: An Encyclopedia of Chemicals, Drugs, and
Biologicals (14th ed.). NJ: Merck, entry 851