# 14 Synthesis of Salicylic Acid From Aspirin Tablets: Drexel Science in Motion
# 14 Synthesis of Salicylic Acid From Aspirin Tablets: Drexel Science in Motion
Introduction:
The reaction below is for an acid-catalyzed hydrolysis. The reactant H2O is in the aqueous
HCl. The other product is acetic acid, the ingredient in vinegar. The hydrolysis of ASA takes
place so easily that a vinegary odor can sometimes be detected in an opened bottle of old
aspirin tablets.
O O
O
C C
OH HCl(aq) OH
+ CH3 COH
OCOCH3 OH
Procedure
Part A: Isolation of acetylsalicylic acid (ASA) from aspirin tablets.
1. Place 50 aspirin tablets in a 250-mL Erlenmeyer flask. Record the mass of acetyl salicylic
per tablet in mg and g from the bottle label. It is not necessary to crush the tablets ahead,
even if they are coated. Add about 50 mL of isopropyl alcohol and warm gently on the low
setting of your hot plate. The alcohol should not be boiling. Swirl the flask from time to
time, until the tablets have all disintegrated. This may take as long as 20 minutes.
2. Using a single coffee filter, filter by gravity into a 500 mL beaker using a clamp on a ring
stand to support the funnel. Wash the residue with a few mL of alcohol. Discard the filter
paper and contents (insoluble binder.)
3. To the alcohol solution that passes through the filter (the filtrate) add about 250 mL of
cold tap water. The acetyl salicylic acid immediately begins to crystallize because it is not
soluble in water-diluted alcohol. Cool in an ice bath for about 5 minutes and/or drop in 3 or
4 ice cubes. When a large amount of solid has appeared and it looks like the crystals have
stopped forming, filter to recover the white ASA. Wash with water to help recover any
crystals sticking to the walls of the filtering flask or beaker.
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4. Remove just a spatulaful, dried first by rubbing on a piece of filter paper. Place in an open
plastic vial to dry. Label this. You will use this sample of ASA in to compare to your next
product, salicylic acid, also a white solid.
5. You will not have time to dry the ASA before proceeding to the next reaction in Part B.
Assuming that the yield for this extraction is 75%, find the amount of ASA isolated from the
50 aspirins. The amount of ASA in one aspirin tablet is 325 mg..
(Keep just 2 significant figures in your answer).
2. When the conversion has taken place you will notice an obvious thickening of the reaction
mixture. Heat for another 10 minutes, then remove from hot plate and allow to cool, using an
ice bath after the flask is no longer hot.
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Name(s) ________________________________________________________________
Complex Formation:
Compound Molecular Appearance Color with Color with
Formula Fe(III) Fe(III) + NaOH
Question:
Assume that you started with 12 g ASA. Can you find the yield of salicylic acid by weighing
it as soon as you finish the filtering step? Explain.
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Instructor’s Guide
#14 Salicylic Acid
(Data and Results)
Complex Formation:
Question:
Assume that you started with 12 g ASA. Can you find the yield of salicylic acid by weighing
it as soon as you finish the filtering step? Explain.
___________________________________________________________________________
The salicylic acid or SA is still wet. It must be dried before the mass of product can be found
and the yield calculated.
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Instructor’s Guide
Salicylic Acid (cont’d)
Time: 1 h
Equipment and Materials per group
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Ideas/ Information
Aspirin tablets each contain 325 mg (5 grains) of acetylsalicylic acid (ASA) and about 50 mg
of inactive starch and cellulose ingredients. Concentrated isopropyl alcohol (91%) will not
dissolve the inactive ingredients.
If desired, this extraction could be done in a single separate lab, so that the ASA could be
dried and weighed before the next reaction. However, we have performed the extraction
many times in our lab and have found the yield to be 75% giving around 12 g ASA. This is
close enough to use in finding the overall yield in the next experiment.
6M HCl solution could be prepared by adding concentrated HCl (12 M) to a volumetric flask
and then diluting with distilled water to the mark on the flask.