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Well, say the synthesis is from p-amino phenol p-H-O-C6H4-NH2. When treated with one equivalent of acetyl chloride or acetic anhydride, the amino group gets acylated selectively. This is because, '-NH2' group is more nucleophilic than '-OH' group. The product obtained initially is paracetamol or acetaminophen, p-H-O-C6H4-NH-COCH3. The conversion of acetaminophen (p-H-O-C6H4-NH-COCH3) into phenacetin (p-C2H5-O-C6H4-NH-COCH3) is an example of the Williamson's ether synthesis (SN2 mechanism) using a phenoxide and ethyl iodide. The net reaction is: p-H-O-C6H4-NH-COCH3 + K2CO3 + C2H5I --->
p-C2H5-O-C6H4-NH-COCH3 + KI + KHCO3
From the starting material phenol, phenacetin can be made in the following manner:

  1. Phenol is nitrated using sulfuric acid and sodium nitrate (as phenol is highly activated, its nitration requires very mild conditions compared to the oleum-fuming nitric acid mixture required to nitrate benzene).
  2. The para isomer is separated from the ortho isomer by fractional distillation.
  3. The 4-nitrophenol is reduced to 4-aminophenol using a reducing agent such as sodium borohydride in basic medium.
  4. 4-aminophenol is reacted with acetic anhydride or acetyl chloride to give paracetamol.
  5. Paracetamol is treated with ethyl iodide in basic medium (Williamson's synthesis) to get phenacetin.

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