Synthesis of 7-hydroxy-4-methyl coumerin from Resorcinol.
Reference:
Furnish B.S, Hanford A.J. "Vogel's Textbook of organic chemistry" longmann scientific and technical UK Ltd. 5th edition 1989 pp 1193.
Requirements
Chemical: Resorcinol, ethyl acetoacetate, conc. Sulphuric acid.
Glassware: RBF, Beaker, glass rod, funnel.
Instruments/Other: ice bath, filter paper, thermometer etc.
Principle:
Resorcinol reacts with Ethyl Acetoacetatecetate under the influence of sulfuric acid to give 7-hydroxy 4-methylcoumarin. Reaction involved in synthesis is Pachmann Condensation Reaction.
Procedure:
Take 15 ml of conc. H,SO, in a flask (50 ml capacity with wide-neck) and stirr it in a ice-bath until the temperature of acid reaches about 5°C. At the same time in another container take 3.7 gm of powdered resorcinol and 4.5 gm of ethyl acetoacetate and mix the contents until a complete solution is obtained. Now add this solution to the sulphuric acid solution very slowly so that the temperature of the mixture does not rise above 10°C, then continue the stirring for 30 min. Pour the mixture on to the crushed ice, when the solid 7-hydroxy-4-methyl coumarin separates. Filter off the coumarin at the pump. Recrystallize the product from ethanol or methylated spirit. The yield of the product is 4.0 gm and its m.p. is 188-190°C.
⬇️⬇️ Vogel's Procedure👇⬇️
USE
Coumarin and coumarin derivatives are examples of anticoagulants. They are widely used to prevent coagulation of blood under certain medical conditions.
Calculations:
Calculate Theoretical Yield
Then find weigh the actual product gained to get Practical Yield.
Calculate percentage yield
%yield= Practical yield ×100
theoretical yield
Result: The product obtained was _____mg/g
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