Question #a86c8

1 Answer
Dec 28, 2016

How about this?


  • Nitration of phenol
  • Reduction of the nitro group
  • Acetylation of the amine

(a) Nitration of phenol

The #"OH"# group is highly activating, so the reaction is carried out at 20 °C.

The 2-nitrophenol is removed by steam distillation.

The 4-nitrophenol is filtered off and purified by recrystallization.

(b) #"NaBH"_4# reduction of 4-nitrophenol to 4-aminophenol

The 4-nitrophenol is reduced to 4-aminophenol at 15 °C by #"NaBH"_4# and #"Pd/C"# in dilute aqueous #"NaOH"#.

(c) Acetylation of 4-aminophenol to paracetamol

The 4-aminophenol is acetylated with acetic anhydride and water at room temperature.

The crude paracetamol is recrystallized from water.