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OF AN ASPIRIN TABLET
Reference: Londa L. Borer & Edward Barry, Journal of Chemical Education, Vol
77, No 3 March 2000
Theory
Aspirin is a common pharmaceutical product used to relieve aches and pains, to reduce
inflammation and to lower fevers. The chemical name is acetylsalicylic acid (ASA). Aspirin is a
weak acid with Ka = 3.27 × 10-4.
O OH
C
O O
C
CH3
acetylsalicylic acid (aspirin)
In most medications, the active ingredient is only a part of the entire capsule. Aspirin is a
relatively old drug; however it is still in use. Some of the current research includes gastrointestinal
effects and its possible use in preventing heart attacks.
In this series of experiments, you will synthesize aspirin and characterize it using TLC and m.p.
Fillers are used to counteract the side effects of the drug. In this lab, the filler is removed and is
tested for the presence or absence of starch.
Procedure
Synthesis and Purification of Aspirin
Aspirin can be prepared by the reaction of acetic anhydride and salicylic acid in the presence of
an inorganic acid as a catalyst. The reaction takes place at the phenol functional group.
O OH O OH
C C
O O O
OH H+ O O
C C C + C
+ H3C OH
H3C O CH3 CH3
1
Weigh ~ 0.42 g of salicylic acid (MW = 138.1) in a small test tube. Add a boiling chip. Add 3 drops
of phosphoric acid followed by 30 drops of acetic anhydride (MW = 102.1, d = 1.08 g/mL). Make
sure to recap the bottle of acetic anhydride. Mix the reactants in a vortex mixer. Cork the test tube
loosely. Clamp the test tube in a water bath (use a 400 mL beaker half filled with water as the
water bath) maintained between 90 ° and 100 °C. The mixture is heated for about 10 minutes. If
all the salicylic acid is not dissolved, add 10 more drops of acetic anhydride. Continue heating for
5 more minutes. Add 2 mL of water dropwise to the mixture and mix well. Cool the test tube to
room temperature. If aspirin crystals do not form, scratch the inside walls of the test tube and then
place the test tube in an ice bath. Filter the crystals using suction filtration. Dry the crystals in an
oven at 100 °C for 20 minutes. Determine the yield of aspirin and its melting point. The reported
melting points of pure aspirin are 135 -136 °C and that of salicylic acid is 159 °C.
2
THE PERCENT COMPOSITION OF AN ASPIRIN TABLET
A. Analysis Of The Theoretical Percent ASA In An Aspirin Tablet
Record the mass of three aspirin tablets separately. Using the stated amount of acetyl salicylic
acid/tablet, calculate the theoretical percent of acetylsalicylic acid in each tablet. Average the
results. What percent of the total weight of the tablet is active ingredient?
3
SYNTHESIS AND CHARACTERIZATION OF ASPIRIN AND %
COMPOSITION OF AN ASPIRIN TABLET
Show work.
Sketch the TLC plate used in this experiment. Label the spots. Comment on the purity of the
prepared aspirin.
4
List the Rf values.
ASA/tablet in g
Theoretical % ASA/tablet