Question

Question #a86c8

Answer 1

How about this?

Explanation:

• 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.