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SYNTHESIS OF CINNAMIC ACID FROM BENZALDEHYDE

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Cinnamic acid is synthesized from benzaldehyde using the Perkin reaction, which involves the condensation of an aromatic aldehyde (benzaldehyde) with an acid anhydride (usually acetic anhydride) in the presence of a basic salt of the acid (typically sodium acetate). This reaction forms an α,β-unsaturated carboxylic acid, namely cinnamic acid. Preparation Steps: Mix benzaldehyde, acetic anhydride, and sodium acetate in a round-bottom flask. Heat the mixture under reflux for 1–2 hours. Cool the reaction mixture and pour it into cold water to precipitate cinnamic acid. Filter the crude product and wash with cold water. Recrystallize from hot ethanol or water for purification. This experiment is a classic method for carbon–carbon bond formation and demonstrates aldol-type condensation under controlled acidic or basic conditions. Keywords: cinnamic acid synthesis Perkin reaction benzaldehyde condensation organic synthesis unsaturated carboxylic acid alpha beta unsaturated acid lab preparation recrystallization

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SYNTHESIS OF CINNAMIC ACID FROM BENZALDEHYDE

AIM:

To prepare cinnamic acid from benzaldehyde

PRINCIPLE:

Cinnamic acid is prepared by using perkin condensation reaction. Cinnamic acid is
prepared by the condensation of benzaldehyde and acetic anhydride in the presence of
sodium acetate as catalyst followed by hydrolysis.The perkin condensation is useful
organic reaction which provide a way to add two carbon atoms to the side chain to the
aromatic ring. Only Non- enolizable aldehyde and ketones can be used.




CHEMICALS REQUIRED:

Benzaldehyde = 5.0 ml

Acetic anhydride = 7.5ml

Sodium acetate = 2.5 g

10% NaOH = Q.S

Conc.HCl = Q.S

PROCEDURE:

Place 5.0 ml of benzaldehyde, 7.5ml of acetic anhydride and 2.5gm of sodium acetate in
round bottom flask.Fit with reflux condenser heat the contents for 1 hour at 70 – 80 c
temperature.After the complete of reaction cool the reaction mixture and add 40.0 ml of
water to it then make the solution alkaline by adding 10 % NaOH solution followed by
acedify the contents with conc.HCl until no more carbon dioxide is liberated.

The cinnamic acid will settle down.Filter the crude sample dry,weigh and calculate the
percentage yield is produced.

, CALCULATIONS:

MOLECULAR WEIGHT OF BENZALDEHYDE

C= 7 x 12 = 84

H= 6 x 1 = 6

O= 1 x 16 = 16

=106

MOLECULAR WEIGHT OF CINNAMIC ACID

C= 9 x 12 = 108

H= 8 x 1 = 6

O = 2 x 16 = 32

=148

THEORTICAL = MOL WT OF THE PRODUCT X WEIGHT OF

YIELD MOL WT OF THE REACTANT REACTANT TAKEN

=------g

PRACTICAL YIELD =------g

PERCENTAGE YIELD = PRACTICAL YIELD X 100

THEORITCAL YIELD

=--------%

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