METHOD :

1 Acidic condition:
i

1.5g of vanillin was added into a conical flask containing 10mL of

acetic acid.

ii

10 drops of 1.0M H2SO4 was added slowly into the solution with stirring.

iii

The mixture then was stirred for 1 hour by using magnetic stirrer at
room temperature.

iv

After the stirring was done, the mixture was placed in cool ice bath for
about 4 minutes.

35mL of ice cold water was added into the mixture, and was shaken to
induce the crystallization.

vi

The mixture was filtered by using Buchner funnel to collect the crystal.

vii

The crystal was washed with 3 portions of 5mL ice cold water.

viii

For recrystallization, 15mL warm ethanol (below 60C) was added with
the crystal collected from the filtration until it dissolved.

ix

The mixture was put in ice bath to initiate the recrystallization.

The mixture was filtered again until dry crystal was obtained.

xi

The weight of product was recorded and the melting point, NMR and
also IR spectra were tested.

2 Basic condition:
i

1.5g of vanillin was added into a conical flask with 25mL of 10% NaOH
solution.

ii

4mL of acetic anhydride and 30g of crushed ice were added into the
solution.

iii

The mixture was shaken for 20minutes and cloudy, milky white
precipitate will form.

iv

The mixture then was filtered by using Buchner funnel with washing of
3 portions of 5mL ice-cold water.

For recrystallization, 15mL warm ethanol (below 60C) was added with
the crystal collected from the filtration until it dissolved.

vi

The mixture was put in ice bath to initiate the recrystallization.

vii

The mixture was filtered again until dry crystal was obtained.

viii

The weight of product was recorded and the melting point, NMR and
also IR spectra were tested.