Northern University Bangladesh
Laboratory Notebook
Course Code: Pharm-3127 & Pharm-4144
Course Title: Medicinal Chemistry-I lab
Medicinal Chemistry-II lab
Submitted To-
Md. Sahab Uddin
Lecturer
Department of Pharmacy (B. pharm)
Northern University Bangladesh
Submitted By-
Name
Full Id
Section
Semester
Batch
Date of Submission: July_____, 2025
Experiment no. 01
Experiment name: Synthesis and analysis of Aspirin (Acetyl salicylic acid)
Principle:
Salicylic acid (o-hydroxy benzoic acid) upon acetylation yields acetyl salicylic acid or aspirin, phenols,
unlike amines cannot be acetylated satisfactorily in aqueous solution. Acetylation proceeds readily with
acetic acid anhydride in the presence of a little concentrated sulfuric acid as catalyst.
Reagents:
Salicylic acid, Acetic anhydride, Conc. sulfuric acid, Alcohol, Water etc.
Apparatus:
Conical flask, Water bath, Beaker, Pipette, Filter paper, Thermometer, Suction pump.
Procedure:
1. 5 gm of dry salicylic acid and 7ml of acetic anhydride was placed in a conical flask.
2. 3 drops of concentrated sulfuric acid was added gradually and the flask was rotated in order to
secure thorough mixing.
3. It was warmed on a water bath to about 50°-60°C stirring with the thermometer for about 15
minutes.
4. The mixture was allowed io coo: end stirred occasionally.
5. 75ml water was added, stirred well and filtered at the pump.
Recrystallisation:
1. This crude acetyl salicylic acid was re-crystallized by dissolving it in a 15ml alcohol followed by
addition of 75ml of hot water.
2. If a solid was separated at this point, the mixture was warmed until solution was completed and
then the clear solution was allowed to cool in a refrigerator.
3. A beautiful needle like crystals would be formed. The crystals were filtered and dried in the
steam oven. The yield of aspirin was calculated.
Calculation:
Molecular weight of salicylic acid=138.12
⸫ Molecular weight of aspirin =180.16
⸫138.12gm salicylic acid yields 180.16 gm aspirin
180.16×5
⸫5 gm salicylic acid yields = ( 138.12
)
= 6.521 gm of aspirin
Theoretical value of aspirin is 6.52 gm
Weight of paper =
Weight of aspirin with paper =
⸫Weight of aspirin =
⸫Practical value of aspirin =
𝑃𝑟𝑎𝑐𝑡𝑖𝑐𝑎𝑙 𝑣𝑎𝑙𝑢𝑒
⸫Yield = 𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑉𝑎𝑙𝑢𝑒 × 100%
⸫Yield of aspirin =
Melting point determination:
❖ The melting point of product was
Spectroscopic analysis:
The spectrum of aspirin was determined by UV spectroscopy in a range of 200 nm to 400 nm. Methanol
was used as a solvent. At first, the absorption spectrum of blank methanol was set to zero. Then a
small amount of aspirin was dissolved in methanol. The spectrum of the solution was observed in UV
spectrophotometer.
Result:
The yield of aspirin was:
Precaution:
➢ All the weights should be determined precisely.
➢ The filtration machine was handled carefully.
➢ The whole drying process should be carried out properly.
➢ The UV spectrophotometer should be handled carefully.
Photo Attachment:
Experiment No. 02
Name of the experiment: Synthesis of Phenacetin
Principle:
Phenacetin is the ethyl ether of p-acetylaminophenol. It can be synthesized by Williamson ether
synthesis reaction in which p-acetylaminophenol is reacted with ethyl iodide in presence of freshly
prepared sodium ethoxide. In the reaction phenacetin is synthesized and equimolar amount of
hydroiodic acid is liberated. Phenacetin synthesized so it not so pure therefore it is recrystallized from
rectified spirit (highly concentrated ethanol containing upto 95.6% ethanol).
Reagents:
p-acetylaminophenol, Ethyl iodide, Sodium metal, Ethanol, Rectified spirit, Water, Decolorizing carbon.
Apparatus:
250 ml round-bottom flask, Beaker, Magnetic stirrer, 10mL measuring cylinder, Reflux condenser,
Water bath, Ice-bath, Buchner funnel and filter paper, Oil bath type melting apparatus, UV-Visible
spectrophotometer.
Procedure:
1. Take a 250mL round-bottom flask, place 30mg of freshly cut pieces of sodium metal in the flask
and dissolve it in 10mL of absolute ethanol.
2. Fit a reflux condenser to the flask.
3. Warm the flask gently in a water bath to complete the formation of sodium ethoxide.
4. After all of solid sodium disappears, heat the solution for few more minutes and then cool it to
room temperature.
5. Add 1.5g of p-acetylamimophenol (Paracetamol) to the flask. Heat the flask again under reflux.
6. Add 1.2mL of ethyl iodide to the flask through the condenser in a dropwise
7. Heat the mixture in the flask under reflux for duration of60 minutes.
8. After 60 minutes of reflux, add 30mL of water to the flask through the condenser at a rate such
that crystals do not separate.
9. Transfer the content of the flask in a beaker and place it in an ice-bath to separate Phenacetin
as crystals.
10. Filter the precipitate in a Buchner funnel and washed it with little cold water. Thus, crude
phenacetin can be obtained.
11. Dissolve the crude product in 10mL of rectified spirit.
12. Add 500mg of decolorizing carbon and then heat the mixture to boiling.
13. Filter the mixture to remove the decolorizing carbon and take the filtrate in a beaker.
14. Add 30mL of hot water to the beaker.
15. Cool the content in the beaker slowly in a refrigerator overnight to allow the phenacetin to
crystallize.
16. The next day, filter the precipitate in Buchner funnel & dry the crystals in air.
Calculation:
Result:
Yield value
Melting point of the product (°C)
UV absorption spectrum of the product,
ƛ(nm)
Comment:
Precautions:
✓ Use freshly prepared sodium ethoxide.
✓ The apparatus should be perfectly dry.
✓ Handle the condenser carefully and monitor the whole time during reflux.
Photo Attachment:
Experiment No. 03
Name of the experiment: Synthesis of Methyl Salicylate
Principle:
Salicylic acid (o-hydroxybenzoic acid) upon esterification yields methyl salicylate, also known as oil of
winter green. Esterification proceeds slowly with methanol and requires the presence of an acid
catalyst.
Reagents:
Salicylic acid, methanol, conc. sulfuric acid, ether/dichloromethane, sodium bicarbonate solution,
anhydrous sodium sulphate, water.
Apparatus:
Boiling chips, Pipette, Graduated cylinder, Spatula, Stirring rod, Beaker, Round bottom flask,
Condenser, Separating funnel, Water bath, Filter paper, Suction pump.
Procedure:
1. Place 5 g of salicylic acid, 50 mi methanol and few boiling chips in a round bottom flask.
2. Add 1.5 mi of concentrated sulfuric acid cautiously to the reaction mixture and mix thoroughly.
3. Reflux the solution for 5 hours.
4. [Link] the excess methanol was removed by evaporation.
5. After the solution cools to room temperature, add 100-150 mL of water to the reaction
6. mixture and extract with ether or dichloromethane (25-30 ml).
7. Allow the layers to separate, and transfer the organic layer, which contains your product, to
another container.
8. Repeat the extraction twice more.
9. Add 25 mi of an aqueous 5% sodium bicarbonate solution to the extract.
10. Mix the solutions together, allow the solvents to separate, end transfer the organic layer to 2
clean, dry beaker.
11. Dry the solution with anhydrous sodium sulfate for 5-10 minutes and filter.
12. Evaporate the filtrate at low heat to obtain the product.
Calculation:
Molecular weight of salicylic acid=138.12
Molecular weight of methyl salicylate =152.15
⸫138.12 gm salicylic acid yields 152.15 gm methyl salicylate
152.15×5
⸫5 gm salicylic acid yields 138.12
gm methyl salicylate
Theoretical mass of methyl salicylate is 5.51 gm
Weight of beaker=
Weight of methyl salicylate with beaker=
⸫Weight of methyl salicylate =
⸫Practical mass of methyl salicylate=
𝑃𝑟𝑎𝑐𝑡𝑖𝑐𝑎𝑙 𝑉𝑎𝑙𝑢𝑒
⸫Yield =𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑉𝑎𝑙𝑢𝑒 × 100%
⸫Yield of methyl Salicylate =
Spectroscopic analysis:
The spectrum of methyl salicylate was determined by UV spectroscopy in a range of 200 nm 400 nm.
Methanol was used as a solvent. At first, the absorption spectrum of blank methanol was set to zero.
Then a small amount of methyl salicylate was dissolved in methanol. spectrum of the solution was
observed in UV spectrophotometer.
Result:
The yield of methyl salicylate was
Precaution:
1. All the weights should be taken carefully.
2. he whole drying process should be performed at low temperature.
3. The UV spectrophotometer should be handled carefully.
Photo Attachment: