UNIVERSIDAD DE ZAMBOANGA

School of Allied Medicine (SAM)

Pharmacy Department
PHARM CHEM – 2 LABORATORY

Name: ___________________ Course/Sec: ___________ Date Submitted: ___________________

Group Name:______________ Schedule: _____________ Date Performed: ___________________
Exercise No. 5
SYNTHESIS OF METHYL SALICYLATE

OBJECTIVE:
To synthesize Methyl salicylate using Salicylic acid and Methanol.

MATERIALS:
Reagents: Apparatus/es:
Salicylic acid Water Bath
Methanol Hot Plate
Hydrochloric acid, 6M Red Litmus Paper
Ferric Chloride T.S. Reflux Condenser
Concentrated Sulfuric acid Cotton Wadding
Sodium Carbonate Solution, 20% Boiling Chips, Beaker
Hexane Erlenmeyer Flask.
Anhydrous Magnesium sulfate Separatory Funnel
Iron Ring, iron Stand

PROCEDURE:

1. Add 60mL of Methanol and a few boiling chips to 27.6g Salicylic acid in a 250mLErlenmeyer
Flask.
2. Carefully add 7mL Concentrated Sulfuric acid to the Mixture.
3. Mix Well by Swirling all the Contents of the Flask.
4. Using a Hot Plate, heat under Reflux for 2 hours.
5. Place the Contents of the Reaction Flask in a beaker and cool in an Ice Bath until the
Contents are below Room Temperature.
6. Slowly add a Small Portion of a 20% Sodium carbonate, constantly stirring, until the Solution
is basic With Litmus Paper.
7. Place the Basic Solution in a 250mL Separatory Funnel.
8. Extract a single 50mL portion of Hexane.
9. Allow the Two Layers to Separate for about 5 Minutes.
10. Drain off the Aqueous Layer from the Separatory Funnel.
11. Wash the Hexane Solution remaining in the Separatory Funnel w/a Single 25mL portion of
water. Drain Water Solution into the Beaker containing the Bulk of the sodium salt of
salicylic acid.
12. Dry the Hexane Solution with q.s. Anhydrous Magnesium sulfate.
13. Evaporate the Hexane on steam bath using Hot Plate in a fume hood.
14. Place the Sample in a properly labelled pre-weighed Vial.
15. Determine the Weight of Methyl salicylate obtained and Calculate the Percentage Yield.

IV. Chemical Reactions Involved: Enumerate All Observed Reactions:

1. _________________________________________________________________

2. __________________________________________________________________

3. _________________________________________________________________
V. DATA :

Actual Yield: ___________________

Theoretical Yield: _______________
Percentage Yield: _______________

VI. COMPUTATIONS:

(Molecular Weight of the Product) (Weight of the Reactants)

Theoretical Yield = -----------------------------------------------------------------------------------------
Molecular Weight of the Reactants

Actual Yield
Percentage Yield = ------------------------------ X 100
Theoretical Yield

VII. Identification Tests:

A. Physical Tests:
1. COLOR : ____________________

2. ODOR : _____________________

3. Appearance : _________________

4. Melting Point: ________________

B. Chemist Tests:
1. Shake 1 drop of Methyl Salicylate with about 5mL of Water and Add 1 Drop of ferric chloride
T.S.
Result: _______________________________________________________________

VIII. CONCLUSION:
IX. QUESTIONS: Provide Substantial answers:

1. What is the Mechanism of Methyl salicylate formation?

2. What are the Natural Sources of Methyl Salicylate?

3. What Method is used in the Extraction of Methyl salicylate from Plants? Discuss briefly. If
you have Data, Explain substantially.

4. Why is the Internal Use of Methyl Salicylate limited to Small Quantities only?

5. Give the Therapeutic Indication of Methyl Salicylate, as well as Its Pharmacological Class
w/Dosage Form Examples.