Dibenzal acetone from Benzaldehyde by Claisen Schmidt reaction

Aim:
To prepare the organic compound Dibenzal acetone from benzaldehyde and acetone in the
presence of sodium hydroxide.

Theory:
Aromatic aldehyde undergoes condensation reaction with aldehyde or ketone which contain
alpha hydrogen atoms in the presence of an alkali. This reaction is called Claisen-Schmidt
reaction. According to claisen aldehydes in the presence of sodium hydroxide can condense
with another aldehyde or ketone eliminating a water molecule. Thus, moles of benzaldehyde
condense with one mole of acetone to give Dibenzal acetone.

The chemical reaction is given below.

Materials Required:
Benzaldehyde
Acetone
Sodium hydroxide solution
Methylated spirit
Dilute hydrochloric acid
Ether
Beaker
Funnel
Conical flask
Filter papers.
Procedure:
Take a conical flask add 10 ml freshly distilled benzaldehyde and 4 ml of acetone.
Place the flask in cold water bath and then add 2.5ml sodium hydroxide drop wise with
constant stirring.
Maintain the temperature at 30oC.
After the complete addition of sodium hydroxide stir the mixture for 2 hours.
Add dilute hydrochloric acid to the reaction mixture and then transfer to a 250ml separating
funnel.
Add 20ml of chloroform/ether to the mixture and shake thoroughly.
Shake the mixture thoroughly, remove the organic layer and repeat the process twice.
Cool the mixture in ice-water. Dibenzal acetone separates initially as a fine emulsion and
then forms yellow crystals.
Distil the residual portion under pressure and collect the fraction boiling at 150oc.
Wash the pale-yellow crystals with cold water, dry and crystallize with ethanol.

Observations:

Colour of the crystals Pale yellow

Expected Yield 4gm

Melting Point 112oC

Calculation
Molecular weight of benzaldehyde is 212g
Molecular weight of dibenzalacetone is 234g
About 5.2g of benzaldehyde shall yield
Dibenzalacetone= [234/212]*5.2 = 5.73g
Theoretical yield is 5.73g
Practical yield is 4g
%yield= [4/5.73]*100 = 69.8%

Results and Discussion:

The yield of Dibenzal Acetone is 69.8%.
Precautions:
Whenever vigorous reaction is taking place inside the flask, release the pressure from time to
time by opening the cork of the flask.
Temperature should not be raised beyond 30oC.
Ethanol and acetone should be kept away from the flame.