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How to Synthesize Hippuric Acid

Hippuric acid can be produced by benzoylating glycine through a procedure involving dissolving glycine in sodium hydroxide, adding benzoyl chloride, adjusting the pH, and crystallizing the product. Instrumental analysis with IR spectroscopy, H1NMR, and mass spectroscopy was used to characterize and confirm the structure of hippuric acid, identifying functional groups and fragments that matched its known molecular structure.

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saad omar
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493 views3 pages

How to Synthesize Hippuric Acid

Hippuric acid can be produced by benzoylating glycine through a procedure involving dissolving glycine in sodium hydroxide, adding benzoyl chloride, adjusting the pH, and crystallizing the product. Instrumental analysis with IR spectroscopy, H1NMR, and mass spectroscopy was used to characterize and confirm the structure of hippuric acid, identifying functional groups and fragments that matched its known molecular structure.

Uploaded by

saad omar
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Making Hippuric Acid

- Introduction:
Hippuric acid is a carboxylic acid and organic
compound found in urine. Levels of hippuric acid
rise with the consumption of phenolic compounds
(such as fruit juice, tea, and wine). The phenols are
first converted to benzoic acid, and then to hippuric
acid and excreted in the urine.
- Procedure:
Hippuric acid can be produced via benzoylation of glycine. 5g of glycine is dissolved in
about 50 ml of 10% NaOH solution and swirled well until all glycine is dissolved. About
7 mL of benzoyl chloride is added to the basic solution of glycine and shook very well until
the oily drops disappeared and the solution becomes crystal clear. Pour the flask contents
into an ice-cold distilled water and adjust the pH value by conc. acid. After about 5-10 min.
the crude product will precipitate out. The solution is filtered off and the ppt is washed,
dried, and purified by recrystallization from boiling water. The product can be confirmed
by measuring the melting point (187 to 188 °C).

- Instrumental Analysis:
1. IR Spectroscopy:
IR spectroscopy is used to identify the functional group in the compound using IR
radiation which causes vibrational transitions of the molecule.
The intense sharp peak at 3342.03 cm-1 in the higher energy region is assigned to NH
stretching mode. The next broadened envelope with the maximum at 3090.37 cm -1 is
assigned to the hydrogen-bonded OH stretch of carboxylic acid. The CH stretch of CH2
is observed at 2938.02 cm-1. There are less intense resolved bands between 2300 and
2700 cm-1 and these are attributed to the hydrogen bonding interaction of the COOH
group in the crystal lattice. The involvement of COOH in hydrogen bonding is also
evident in the above said molecular packing diagram of the unit cell. The intense sharp
peak at 1744.3 cm-1 is due to the C=O stretching of COOH. The aromatic ring skeletal
vibrations and C–N stretching vibrations are positioned at 1603.52, 1556.27, and
1489.74 cm-1. The CH2 bends are observed at 1395.25 and 1416.46 cm-1.
2. H1NMR:
Nuclear magnetic resonance detects the structure of the chemical compound using radio
frequency radiation which causes nuclear spin for the protons. The last peak at the left
for the carboxylic acid hydrogen while that at 8 ppm for N-H. At 7.5 ppm the phenyl
ring and at 3.6 ppm is -CH2- protons.

3. Mass spectroscopy:
Mass spectroscopy is used to determine the Mwt and molecular formula of the
compound by fragmentation of it with an electron beam. From the Mwt of these
fragments, the Mwt and formula were detected.

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