The document describes the procedure for preparing acetanilide from aniline. Specifically, it involves: 1) Dissolving aniline in hydrochloric acid and water to form a clear solution. 2) Adding acetic anhydride and sodium acetate to this solution, which results in the acetyl group replacing the active hydrogen in aniline's amino group to form acetanilide. 3) Precipitating the acetanilide product, filtering it, washing it with cold water, and crystallizing it with boiling water and methanol to obtain the final purified acetanilide. Yield is determined by comparing actual and theoretical amounts based on amounts of reactants used.

1. Objective: Preparation of Acetanilide from
Aniline.
Mrs Chanda Ranjan
Dept of Pharm Chemistry
The Oxford College of Pharmacy

2. Objective: Preparation of Acetanilide from Aspirin
• Chemicals Required: Aspirin, acetic anhydride, sodium acetate, conc hydrochloric
acid, water and methylated spirit.
• Apparatus Required: Beaker, conical flask, funnel, stirrer, and pipette.

3. Principle:
• Acetanilide is an odorless solid chemical of leaf or flake-like appearance.
Acetanilide was the first aniline derivative found to possess analgesic as well as
antipyretic properties.
• Acetanilide is prepared by acetylation of aniline with acetic anhydride and in
the presence of sodium acetate and hydrochloric acid.
• The active hydrogen atom present in the amino group is replaced by the by the
acetyl group of acetic anhydride in the presence of sodium acetate and forms
Acetanilide.
Reaction Involved

4. Mechanism Involved
Principle:
• Acetanilide is prepared by acetylation of aniline with acetic anhydride and
in the presence of sodium acetate and hydrochloric acid.
• The active hydrogen atom present in the amino group is replaced by the by
the acetyl group in the presence of sodium acetate and forms Acetanilide.

5. 1. About 4 ml of Aniline was taken and added to 3.7 ml of conc HCl dissolved in 100 ml of
water
4 ml of Aniline
3.7 ml conc HCl +
100 ml of water
2. The mixture is stirred until a clear solution is obtained.
Procedure
Stir well to get a
clear solution

6. 3. To the clear solution 5.3 ml of acetic anhydride was added and stirred.
5.3 ml of acetic anhydride 5.7 gm sodium acetate dissolved
in 20 ml of water
4. Then a crystalline sodium acetate (5.7 gm.) in water 20 ml was also added and stirred.
Procedure
Stirred well

7. Ice cubes are added
Stir well
5. To the mixture ice was added to it and stirred vigorously
6. Acetanilide was separated
Procedure

8. The precipitate
obtained of acetanilide
is filtered
7. Acetanilide was filtered.
Procedure
cold water
8. The obtained acetanilide was washed with cold water.

9. crystallized with boiling water
containing 2-5 ml methylated sprit
Crude Acetanilide
9. Crystallized with cold water containing methylated spirit (10 % methanol).
Procedure
10. The obtained compound will be weighed and melting point will be
determined and practical yield will be calculated.

10. Calculation
• Molecular weight of Aniline= 93 gm (1.02 g/cm³)=91.176 ml
• Molecular weight of Acetanilide= 135 gm
• 91.176ml of Aniline gives--- 135 gm of Acetanilide
• Therefore, 4 ml of Aniline will give---- 5.92 gm of Acetanilide
(theoretically)
• Percentage yield= Practical Yield x 100
---------------------
Theoretical yield

11. •Thank You