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Sodium phenoxide is heated with CO2 under pressure at about 125 deg C (Kolbe-Schmitt reaction) and the product is then acetylated. What is the major final product C?

1. Aspirin (acetylsalicylic acid)
2. Salicylaldehyde
3. Methyl salicylate
4. Benzoic acid

Correct answer: Aspirin (acetylsalicylic acid)

Solution

Kolbe-Schmitt gives salicylic acid (2-hydroxybenzoic acid); acetylating its phenolic -OH with acetic anhydride yields acetylsalicylic acid, i.e. aspirin.

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