The Synthesis of Aspirin

Purpose: To synthesize aspirin, a common analgesic drug. The experiment

actually involves three parts: The synthesis of aspirin, the isolation and
purification of aspirin, and the estimation of the purity of the final product.
Synthesis: The synthesis involves the reaction of salicylic acid and acetic
anhydride in the presence of a catalyst, phosphoric acid, H 3PO4.

Isolation and Purification: Once the aspirin is prepared it must be isolated

from the reaction solution and purified. The aspirin is insoluble in cold water,
and can be isolated by filtering the chilled reaction solution. Purification is
necessary to remove any unreacted salicylic acid and acetic anhydride, as well
as the acetic acid product and phosphoric acid. Acetic anhydride is caused to
decompose by the addition of water once the formation of aspirin is complete:

The acetic acid and phosphoric acid are water soluble and can be removed by
washing the aspirin with chilled water. Salicylic acid is only slightly soluble in
water and is not completely removed in the washing step. Final purification is
accomplished by the process of recrystallization. The impure aspirin is
dissolved in warm ethanol. The solution is then cooled slowly, and the aspirin
crystallizes out of solution leaving the salicylic acid and other impurities
behind.
Estimation of Purity: The melting point of a compound can be used to
identify it and also to estimate its purity. Generally an impure compound will
exhibit a melting point which is lower than that of the pure compound.
Therefore, if your aspirin melts at a temperature below the accepted melting

point two possibilities exist: either your product is impure or it is not aspirin. A
pure substance will melt sharply over a range of 1 or 2 degrees celcius. That is,
the temperature at which melting first occurs is only 1 or 2 degree less than the
temperature at which the sample is completely melted. An impure compound
will melt over a wider temperature range.
Safety Considerations: This experiment uses salicylic acid, acetic anhydride
and phosphoric acid. The salicylic acid and aspirin may cause irritation to your
skin or eyes, but are basically not hazardous. An excess of these can be
disposed of in the sink or if packaged, in the trash. If you spill some, wipe it up
with a wet paper towel and throw the towel in the trash. The acetic anhydride
and phosphoric acid can cause bad burns. Use them in the hood. Be sure to
wear gloves and safety goggles when using these chemicals. Excess chemicals
must be disposed of in the plastic tub of water. This will convert the acetic
anhydride to vinegar and dilute the phosphoric acid. If you spill a lot of either
of these, notify your instructor.