46 CHE 214L Laboratory Manual Spring 2021
EXPERIMENT #3A
The Williamson Ether Synthesis:
Conversion of Acetaminophen into Phenacetin
Adopted from: Palleros, D.R. Experimental Organic Chemistry;
John Wiley & Sons, Inc.: Hoboken, 2000.
Macroscale Reaction Set-Up
1. Place 6.6 mmol of acetaminophen in a dry 25 or 50 mL round bottom flask along
with a magnetic stir bar or a couple of boiling chips.
2. Carefully add 2.4 equivalents of ethyl iodide via pluringe to the flask, followed by 1.4
equivalents of potassium carbonate and 24 equivalents of butanone.
3. Set up the flask for heating under reflux. Reflux for one hour.
Extraction
4. After one hour, remove the flask from the heat and allow the solution to cool to
room temperature. Transfer the solution to a small separatory funnel.
5. Rinse the flask with 10-20 mL of water and transfer the contents to the separatory
funnel. Then rinse the flask 4 times with 3-5 mL of t-butyl methyl ether (TBME) and
add each rinsing to the separatory funnel.
6. Extract the mixture and remove the aqueous layer into another flask. Extract the
aqueous layer with 5-10 mL of TBME and combine with the previous organic layer.
7. Extract the combined organic layers twice with 5-10 mL of 5% aqueous NaOH,
followed by 5-10 mL of brine. Dry the organic layer over magnesium sulfate.
8. Filter and place the solution into a pre-tared 100 mL round bottom flask. Remove
the solvent via rotary evaporation. Mass the product.
Recrystallization
9. While swirling the flask in a hot water bath, completely dissolve the solid in a
minimum amount of ethyl acetate in a 50 mL Erlenmeyer flask, and add hexanes
drop-wise until the solution becomes cloudy. Allow the flask to cool to RT followed
by cooling in an ice-water bath.
Filtration & Characterization
10. Filter the solid under vacuum. Mass the product. Determine the melting point.
Obtain an IR, 1H NMR, 13C NMR, and TLC (ethyl acetate).
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CHE 214L Laboratory Manual Spring 2021 47
11. Perform ferric chloride test for phenols on the starting material and product. Place
1 mL of a 0.1% aqueous solution of ferric chloride in each of four, small, labeled
test tubes. Add a small amount of acetaminophen, your product, and salicylic acid
into three separate test tubes. Observe a color change. Colors ranging from green
to red are considered a positive test, while yellow is negative. – EOC Unit 15
Boogieman
48 CHE 214L Laboratory Manual Spring 2021
PRE-LAB QUESTIONS FOR EXPERIMENT #3A
The Williamson Ether Synthesis:
Conversion of Acetaminophen into Phenacetin
Unit 15 (read pages 323-325 of Experimental Organic Chemistry)
Introduction: Make sure you address each of the questions below when writing your
Introduction. Although for the pre-lab you may answer the questions separately, in your
final report, all of these points must be addressed in paragraphs, in a clear, cohesive,
and logical fashion.
1. Concisely summarize both the objective and purpose for Experiment #3A.
2. Draw the electron-pushing arrow mechanism for the reaction performed in
Experiment #3A.
Experimental: You are not required to add an Experimental Section to your final
laboratory report. However, you must still answer these questions regarding your
experimental procedure in your pre-lab.
3. Draw a flow chart that clearly outlines how the primary product of your reaction will
be separated from the reaction mixture and isolated. The flow chart should include
all organic and aqueous extractions, and when applicable, denote which layer is the
top layer and which is the bottom layer. Intermediary boxes should include the
specific chemical(s) that are in that layer.
4. The Williamson ether synthesis is a simple two-step (1) acid/base reaction followed
by a (2) nucleophile/electrophile reaction. Why are they very useful for benzyl halide
and primary alkyl halide electrophiles, but often fail for secondary, tertiary, and aryl
halide electrophiles? What products might you expect if your electrophile in this
reaction was i-PrBr?.
Results & Discussion:
5. For each characterization test you will perform, provide one specific piece of data
that will indicate that your objective was fulfilled, and the expected product(s) were
obtained. For each piece of data, explicitly state whether it shows that your reaction
(a) went to completion, and/or (b) proceeded to give the expected product.
6. For what functional group will the ferric chloride test provide a positive result?
Draw a scheme of the ferric chloride reaction, and show how it would provide a
positive or negative result. At the end of the first week’s reaction (Williamson Ether
Synthesis), do you expect your ferric chloride test to be negative or positive?
7. Discuss the “greenness” of this etherification reaction, specifically with respect to
energy efficiency and waste prevention.
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