Two widely used pain relievers are aspirin and acetaminophen. Show how you would synthesize these drugs from phenol.

Verified step by step guidance

1. Step 1: Begin with phenol (C₆H₅OH) as the starting material. Phenol has a hydroxyl (-OH) group attached to a benzene ring, which can be functionalized to create both aspirin and acetaminophen.
2. Step 2: To synthesize acetaminophen, first convert phenol into para-aminophenol. This can be achieved by nitration of phenol to form para-nitrophenol, followed by reduction of the nitro group (-NO₂) to an amine group (-NH₂).
3. Step 3: Acetylate the para-aminophenol by reacting it with acetic anhydride (CH₃CO)₂O. This introduces the acetyl group (-COCH₃) to the amine group, forming acetaminophen (C₆H₄OHNHCOCH₃).
4. Step 4: To synthesize aspirin, first convert phenol into salicylic acid. This can be done by Kolbe-Schmitt reaction, where phenol reacts with carbon dioxide (CO₂) under basic conditions to form salicylic acid (C₆H₄OHCOOH).
5. Step 5: Acetylate salicylic acid by reacting it with acetic anhydride (CH₃CO)₂O. This introduces the acetyl group (-COCH₃) to the hydroxyl group, forming aspirin (C₆H₄COOHCOCH₃).

Key Concepts

Phenol

Phenol is an aromatic compound characterized by a hydroxyl group (-OH) attached to a benzene ring. It serves as a key starting material in organic synthesis, particularly for the production of various pharmaceuticals, including aspirin and acetaminophen. Understanding its reactivity and functional group transformations is essential for synthesizing these drugs.

Acetaminophen Synthesis

Acetaminophen, or paracetamol, can be synthesized from phenol through a two-step process: first, phenol is converted to an aniline derivative via nitration and reduction, followed by acetylation of the amine group. This process highlights the importance of functional group transformations in organic synthesis, particularly in drug development.

Aspirin Synthesis

Aspirin, or acetylsalicylic acid, can be synthesized from phenol by first converting it to salicylic acid through a hydroxylation reaction, followed by acetylation of the hydroxyl group. This synthesis pathway illustrates the significance of esterification reactions in organic chemistry, particularly in the context of creating analgesic compounds.