ChemicalBook CAS DataBase List Hippuric acid

Hippuric acid synthesis

10synthesis methods

Product Name:Hippuric acid
CAS Number:495-69-2
Molecular formula:C9H9NO3
Molecular Weight:179.17

Preparation of Hippuric acid from Glycine.
Principle: The hydroxy and amino functions can be easily benzoylated using Benzoyl chloride in aqueous alkaline conditions. This reaction is known as Schotten-Baumann reaction.
Reaction:

Procedure: Dissolve 0.5 g of glycine in 5 ml of 10% NaOH solution in a 25 ml conical flask. Add 0.9 ml of benzoyl chloride in five portions to the solution. Stopper the flask and shake vigorously after each addition until all the benzoyl chloride is reacted. Transfer the solution to a beaker and add few grams of ice and add conc. HCl slowly with stirring until the solution is acidic to litmus paper. Filter the crystalline precipitate of the product on a Buchner funnel, wash with cold water and drain well. Place the solid in a conical flask with 10 ml CCl4 and boil gently for 10 min. Allow the mixture to cool slightly, filter under gentle suction and wash with 10-20 ml CCl4. Record the practical yield and re-crystallize it.
Re-crystallization: Dissolve the crude product from boiling water (5 ml), with addition of decolorizing charcoal if necessary, filter the hot solution and cool the filtrate. The crystals of the product separate out. Filter, dry and record the melting point and TLC [using Butanal : acetic acid: water (4 : 1 : 1) as solvent or CHCl3:methanol (9 : 1) or toluene].

98-88-4 Synthesis

98-88-4
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$10.00/5g

56-40-6 Synthesis

56-40-6
1362 suppliers
$5.00/25g

495-69-2
452 suppliers
$7.00/25g

Yield:495-69-2 96%

Reaction Conditions:

with sodium hydroxide in lithium hydroxide monohydrate;

References:

Mesaik, Muhammad A.;Rahat, Shagufta;Khan, Khalid M.;Zia-Ullah;Choudhary, Muhammad I.;Murad, Shahnaz;Ismail, Zakiah;Atta-ur-Rahman;Ahmad, Aqeel [Bioorganic and Medicinal Chemistry,2004,vol. 12,# 9,p. 2049 - 2057]

56-40-6 Synthesis

56-40-6
1362 suppliers
$5.00/25g

100-51-6 Synthesis