Reduction of Vanillin to Vanillyl Alcohol

H
H O H OH
MW 37.83

1. NaBH4, NaOH

2. H3O+
OCH3 OCH3

OH OH

Vanillin Vanillyl Alcohol

MW 152.15 MW 154.06
C8H8O3 C8H10O3

Responsible for the Perfume: Coconut,

flavour and aroma cream, milk, balsam
of vanilla
 “ H ”: Nucleophile or Base?

LiH Li H Li X = 0.98
Na X = 0.93 Ionic
NaH Na H H X = 2.20

⇒ Source of basic, non-nucleophilic “ H ”

LiAlH4 Li AlH4 B X = 2.04

Al X = 1.61 Covalent
NaBH4 Na BH4 H X = 2.20

⇒ Source of nucleophilic, non-basic “ H ”

Na B
H
H
H
Reaction Mechanism
 Reaction Mechanism

Pay attention to stoichiometry when determining the limiting reagent!

 TLC Analysis: Monitoring the Progress of the Reaction

1: Vanillin + NaOH
2: After complete addition of NaBH4
3: 10 mins after complete addition of NaBH4

2 1 3 Apply all three spots before developing the plate!

(visualise the plate under the UV lamp)

Solvent system ethyl acetate : hexane : acetic acid

2 mL : 2 mL : 2 drops

Solo: Use a 100 mL beaker

Pairs: Use a 250 mL beaker and double solvent volumes
 Tips and Reminders

1. When spotting the TLC plate, use a fresh capillary tube for each spot

2. Don’t forget to check the pH of the solution after 5 minutes!

3. Use the water aspirator as the vacuum source for isolating the crude product (once
the bulk of the filtrate has been collected, empty the Buchner flask and use the
house vacuum to get the crude product completely dry).

4. Record the crude mass and M.P.

5. No purification will be undertaken. Base all of you percent yield calculations on

crude product mass.

6. Hand in a report of results. Note that there will be a quiz on this experiment,
written during experiment 5