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JEE Main · 2014 · 06 Apr 2014 · Offline · Alcohols Phenols and Ethers

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Sodium phenoxide when heated with CO₂ under pressure at 125°C yields a product which on acetylation produces C.

The major product C would be:
  1. (A)(see structure)
  2. (B)(see structure)
  3. (C)(see structure)
    ✓ Correct
  4. (D)(see structure)

Answer: (C)

Solution

Heating sodium phenoxide with carbon dioxide under pressure is the Kolbe-Schmitt reaction, and the carboxyl group enters ortho to the oxygen to give salicylate, that is salicylic acid after work-up. Acetylating the phenolic then caps it as an acetate, so the major product C is 2-acetoxybenzoic acid, ordinary aspirin.

JEE Main · 2014 · 06 Apr 2014 · Offline · Single correct option

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