Synthesis of Aspirin

(Acetylsalicylic Acid)

Organic Chemistry II
May 13, 2003

Jamie Yeadon
Shannon Land
Leah Monroe
 Acetylsalicylic Acid
O
O C CH3
Ester Formula Weight:
180.16 g/mol
Melting Point:
COOH 135°C
Carboxylic acid
Aromatic Ring
 Aspirin History
•Discovered by Dr. Felix Hoffmann in 1897
•Was searching for remedy for his father
-suffered from rheumatoid arthritis
• In US: 300 tablets per year for each man
woman, and child are produced
• Is helpful in small doses of 0.3 – 1 g
In large doses - Fatal
 Aspirin – How it Works

•Analgesic – for pain relief

•Anti-inflammatory agent
•Antipyretic compound – reduces fever
•Inhibits body’s production of prostaglandins
 hormone-like substances
 regulate pain, fever, inflammation, and
obstruction of blood vessels by thrombi
 Procedure
Synthesized Product
1) Mix Salicylic acid and Acetic Anhydride
2) Catalyze reaction with Sulfuric acid
3) Apply heat until solution is formed
4) Add water, then cool
5) Collect crystals via vacuum filtration
6) Recrystallize using 95% ethanol
 Procedure
Commercial Product
1) Crush 4 commercial tablets (325 mg/each)
2) Add 4 mL 95% ethanol
3) Apply heat until solution is formed

4) Allow to cool, then put in ice bath

5) Collect crystals via vacuum filtration
 Overall Reaction
COOH
O O
H2SO4
+ CH3 C O C CH3
OH
Acetic Anhydride
Salicylic Acid
O
O C CH3

+ CH3COOH

COOH Acetic Acid

Acetylsalicylic Acid
(Aspirin)
 Calculations
Limiting Reagent:
Salicylic Acid

Theoretical Yield: 4.565 g

Product Yield: 3.123 g

Percent Yield: 68.40%
 Melting Point Analysis

Synthesized Product: 128 - 130 °C

Commerical Product: 127 - 136°C

Literature Value: 128 - 137°C

 Infrared Spectroscopy
Synthesized Commercial
Product Product

1605.75 cm-1 Benzene Ring 1605.67 cm-1

3016.31 cm-1 Aromatic No Signal
–CH bonds
2500-3100 cm-1 -COOH group 2500-3100 cm-1

755.53 cm-1 o-substituted 755.88 cm-1

Benzene
 Infrared Spectroscopy
Library Matches
(Nicolet and Georgia Crime Lab)

With Acetylsalicylic Acid:

Synthesized Product: 86.92%
Commercial Product: 87.68%
Nuclear Magnetic Resonance
Spectroscopy
Synthesized Product
Nuclear Magnetic Resonance
Spectroscopy
Commercial Product
Ultraviolet Visible Spectroscopy
Synthesized Commercial
Product Product

275.5 cm-1 Benzene Ring 275.5 cm-1

230.5cm-1 -COOH group 233.5 cm-1

215.5 cm-1 -COO in ester 221.5 cm-1

 Overall Analysis
Melting Point Analysis Both Product
Identities
Infrared Spectroscopy Confirmed
To be

NMR Spectroscopy Acetylsalicylic

Acid

UV Visible Spectroscopy