Synthesis of p-chlorophenoxyacetic acid

Amanda Ivester

Organic Chemistry 2280, Section 6

Instructor: Heeren Gordhan
March 10th, 2014

Abstract
The goal of this experiment was to synthesize p-chlorophenoxyacetic acid. This synthesis
was accomplished through an SN2 reaction, recrystallization, and vacuum filtration. Testing of
the crystals that were synthesized indicated a melting range of 157-159C. The yield of the
synthesized crystal was 1.97g. This yield corresponded to a percent yield of 21.27% of the
expected amount of product, which was 9.26g. The synthesized compound had an identical
melting range to a known sample of p-chlorophenoxyacetic acid. Both the synthesized
compound and the known sample of p-cholorophenoxyacetic acid exhibited FTIR peaks at 1700,
1200, 1600 to 1400, and 800 corresponding to the appropriate C=O, C-O, Benzene, and C-Cl
bonds respectively. This two results conclusively showed that the synthesized product was pcholorophenoxyacetic acid.
Introduction
The purpose of this experiment was to synthesize p-chlorophenoxyacetic acid, a synthetic
plant hormone used to influence the growth of plants3. Para-chlorophenoxyacetic acid can be
easily synthesized through an SN2 reaction of a 4-chlorophenolate anion and with a chloroacetate
anion. The experiment consisted of a nucleophilic substitution reaction, recrystallization, and
vacuum filtration. The product was later confirmed to be p-cholorophenoxyacetic acid through
melting point and FTIR comparisons. The synthesized compound had an identical melting range
to a known sample of p-cholorophenoxyacetic acid, indicating that the synthesized sample was
pure. FTIR comparison shows a small bit of contamination in the synthesized sample, as
indicated by an unexpected peak at ~2200.
Results
Table One: Experimental Observations
Time During Experiment
Before any heating
During first heating
During second heating
After second heating
After vacuum filtration

Description
Pale yellow powder
Milky white liquid
Yellow mostly translucent liquid
Pale yellow liquid with white crystals
White powder/crystal

Table Two: Melting point of p-chlorophenoxyacetic acid

Expected1
157-159C
Observed
157-159C
Table Three: Yield in Grams of p-chlorophenoxyacetic acid
Theoretical
9.26g
Observed
1.97g
Percent
21.27%
Figure One: Percent Yield Formula
Actual Yield of Product Grams
100=Percent Yield of Product
Theoretical Yield of Product Grams

Figure Two: Theoretical Yield of p-chlorophenoxyacetic acid

5.0 g
100=54 X=9.26 g
X
Figure Three: Percent Yield of p-chlorophenoxyacetic acid
1.97 g
100=21.27 Figure Four: Structure of p-cholorphenoxyacetic acid
9.26 g

Figure Five: Known NMR of p-chlorophenoxyacetic acid

Peak Number
1
2-6

Proton
Acidic Proton
Aromatic Protons

7-8
H-C-O Protons
Figure Six: Known FTIR of p-chlorophenoxyacetic acid

Figure Seven: FTIR of Experiment Synthesized p-chlorophenoxyacetic acid

Peak Number
~1700
~1200

Bond
C=O
C-O

1600-1400
~800
Discussion

Benzene
C-Cl

Table One describes various physical observations throughout the experiment.

Table Two indicates the results of initial melting point testing on the synthesized
compound. The typical recorded melting range for p-chlorophenoxyacetic acid is 157-159C1.
Upon testing, the observed melting range of the synthesized compound was indeed 157-159C,
offering further indication that the synthesized compound was p-chlorophenoxyacetic acid as
intended.
Table Three indicates the various yields of the synthesized compound while Figures
One through Three show the mathematical explanation for how these numbers were determined.
Had the experiment gone perfectly, which is impossible, 9.26g of p-chlorophenoxyacetic acid
would have been derived. According to standard lab procedures, 5.0g (a 54% yield) is considered
a good result2. During this particular experiment, only 1.97g (21.27% yield) were derived.
Reasons for the low yield include poor crystal formation during recrystallization and loss of
crystals during vacuum filtration.
Figure Five shows a known NMR of p-chlorophenoxyacetic acid. Due to laboratory
problem, an NMR for the synthesized compound was unable to be obtained; however, due to
other results it was still able to be reasonably concluded that the synthesized compound was pchlorophenoxyacetic acid. Had an NMR of the synthesized compound been completed, it would
have been expected to see peaks corresponding to both benzene protons and H-C-O protons.
Figure Six shows a known FTIR of p-chlorophenoxyacetic acid and Figure Seven shows
an FTIR of the synthesized compound. Discrepancies between the FTIRs are minimal and major
peaks only differ by insignificant amounts. All of the major peaks listed in Figure Seven
correspond to bonds expected to be present in the structure of p-cholorphenoxyacetic acid shown
in Figure Four. There is, however, an unexpected peak at ~2200 which more than likely
corresponds to a C=C bond which is still consistent with the synthesized compound being pcholorophenoxyacetic acid.
Conclusion
At the conclusion of the experiment, 1.97 grams of product was synthesized. This
corresponded to a 21.27% yield. The synthesized product showed a melting range of 157-159C.
This melting range was identical to a known sample of p-chlorophenoxyacetic acid when
compared. The FTIR of the synthesized compound matched very closely with a known FTIR of
p-cholorophenoxyacetic acid, with both FTIRs exhibiting peaks at 1700 (C=O), 1200 (C-O),
1400 to 1600 (benzene), and 800 (C-Cl). The two results confirmed that the synthesized
compound was in fact p-cholorphenoxyacetic acid and that the goal of this experiment had been
accomplished.
Experimental
1. In a 125mL Erlenmeyer flask, add 50mL of sodium chlorophenolate
2. Add 9.5g of chloroacetic acid
3. Swirl flask to dissolve solid
4. Place the liquid on a steam bath for 30 minutes
5. Allow the flask to cool to room temperature
6. Place the flask in an ice bath for 3 to 5 minutes

7. Add 40mL of HCl 5mL at a time over the course of 2 to 3 minutes, swirling to
incorporate
8. Place the flask in an ice bath once again for an additional 3 to 5 minutes
9. Vacuum filter, washing with 10mL cold water
10. In a separate beaker, mix 10mL cold water and 10mL ethanol
11. In a 125 Erlenmeyer flask, mix the vacuum filtered solid with the water/ethanol mixture
12. Heat the flask on a steam bath until all solid is dissolved
13. Allow the flask to cool to room temperature
14. Place the flask in an ice bath for 3 to 5 minutes
15. Vacuum filter the solution
16. Allow the solid to continue to air dry for further testing at a later date
References
1. 4-Chlorophenoxyacetic acid. (n.d.). ChemicalBook---Chemical Search Engine. Retrieved
February 15, 2014, from
http://www.chemicalbook.com/ChemicalProductProperty_EN_CB7189313.htm
2. Ch 2280. (n.d.). chemistry.clemson.edu. Retrieved February 15, 2014, from
http://chemistry.clemson.edu/organic/Labs/2280Docs/Chloroacetic.pdf
3. Reregistration EligibilityDecision(RED) 4-Chlorophenoxy-acetic Acid (4-CPA). (1997, March
1). www.epa.gov. Retrieved February 14, 2014, from
http://www.epa.gov/oppsrrd1/REDs/2115red.pdf