Procedure

Preparation oI 4-Acetyl-3-Methoxybenzaldehyde
1.5 g oI vanillin is dissolved in 25ml oI 10 sodium hydroxide in a 250 ml Erlenmeyer Ilask.
30 gram oI crushed ice and 4ml acetic anhydride is added. The Ilask is stopper with a clean
rubber stopper and shake several times over a 20 minutes period. The precipitate is Iiltered using
Buchner Iunnel and washed with three 5 ml portion oI ice cold water.
The solid Iorm oI 95 ethyl alcohol is recrystallized.The mixture is heated in a hot water bath
about 60 Celcius to avoid melting the solid. The crystals are weigh and the percentage yield is
calculated.The melting point is calculated. The inIrared spectrum is determine using the dry Iilm
method.
EsteriIication oI Vanillin in the presence oI acid
1.5 g oI vanillin is dissolved in10 ml oI acetic anhydride in 125 ml Erlenmeyer Ilask. A magnetic
stir bar is placed in a Ilask and the mixture is stirred at room temperature until dissolve. 10 drops
oI 1 M sulIuric acid is added to the mixture . The Ilask is stirred at room temperature Ior 1 hour.
Then the Ilask is cooled in ice water bath Ior 4-5 minutes. 35 ml oI ice water is added to the
mixture in the Ilask. The Ilask is stopper ed and shake vigorously. Crystallization occur in 10-15
minutes. The product is Iiltered and wash with three 5ml portions oI ice cold water.
The crude product is recrystallized Irom hot 95 ethanol.The crystal is allowed to dried.The
crystal is weigh and the percentage yield is calculated and the melting point is determine.






.
O
O
O
Acetic anhydride
O
H
O
O CH
3
O H
H
O
O
O
O
H
O
O
CH
3
O
H
H
Mechanisme under basic condition
O O
O CH
3
O H
O
O
O
H
H
Vanillin
O
O
O CH
3
O H
O
H
H
O
O
CH
3
+
+
+
+
+
+
+

hile the reaction oI vanillin in the presence oI acid yield a diIIerent observation.During
stirring, the color changes Irom colorless to purple orange .A diIIerent structure Iormed and is
proven Irom the analysis oI IR and NMR spectrum.Melting point obtained is 91 Celcius,which is
in between the theoretical value 90 Celcius to 91 Celcius.
Mechanisme under the acid condition
O
O
O
H
O
O
CH
3
O
H
O
H
H
H
-
Acetate anhydride
Vanillin
O
O
O
H
H
O
O
CH
3
O
H
O
H
H
O O
O CH
3
O H
O
O
O
H
H
H
H
H
O
O
CH
3
O
O
O
H
O
O
H
H
H
H
O
O
CH
3
O
O
O
H
O
Vanillin Acetate
+
+
+
+
+
+
+