PREPARATION OF P-ACETYLAMIDE PHENOL FROM P-A

PREPARATION OF P-ACETYLAMIDE PHENOL FROM P-Aminophenol

Theory:

It is also known as Paracetamol or acetaminophen. Paracetamol is a Chance discovery. The distinctive properties of Paracetamol were discovered by an accident. Chemist took interest to modify its structure aim to find a compound that was less harmful.

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Uses:

  • It is a medicine which is being widely used to treat pain and fever. It is usually being used for mild or moderate pain relief
  •  Paracetamol is also being used for severe pain, such as cancer pain and pain after surgery
  •  It is typically used either by mouth, but sometimes it can be used rectally
  • It is also available in liquid phase to inject in the body by injection into a vein.
  • Usually its Effects last for two and four hours duration

Abuses:

  • Paracetamol is generally safe at recommended doses. For an adult the recommended maximum daily dose is three to four grams and further concentration may cause serious outcomes
  • Higher dose also cause serious skin rashes
  • The patients of liver disease can use it but in lower dose

Para-aminophenol:

4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the chemical formula H2NC6H4OH. It is typically available as white powder.

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Procedure:

  • First of all 6 g of p-aminophenol is weighed and transferred to a 100ml conical flask which should be thoroughly cleaned and dried
  • Add 6.5 ml of acetic anhydride to the flask and 3-4 drops of concentrated sulphuric acid carefully
  • The contents of the flask should be mixed thoroughly
  • The mixture should be warmed on a water-bath maintained at 60°C for about 20-25 min with constant stirring
  • Now allow the flask to attain room temperature, and pour it directly into a beaker containing 100ml of cold water and stir it vigorously
  • The crude product obtained is filtered by using a Buchner funnel using suction, then wash it with cold water
  • Drain the water well and dry the product by using the folds of filter paper or in air-dry
  • The yield of end product i.e. paracetamol is approximately 6.8 g

Recrystallization:

  • Now dissolve the end product in 70% (v/v) ethanol and warm it up-to 60°C. And then 2 g of powdered animal charcoal is added as a decolorizing reagent.
  • Filter the solution and concentrate the filtrate over a water-bath to remove excess water through heating
  • Now allow it to cool and large monoclinic crystals are separated
  • The yield of the pure paracetamol is 6.5 g whose melting points are 169-170.5°C

Reactions:

Synthesis of p-Aminophenol

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Synthesis of P-Acetylamide Phenol

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Mechanism:

P-Aminophenol

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P-Acetylamide Phenol:

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Paracetamol

Examples:

  • Acedoben synthesis:
  • Metacetamol synthesis:

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PREPARATION OF P-ACETYLAMIDE PHENOL FROM P-Aminophenol

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