In a reaction sequence, sodium phenoxide reacts with CO_2 under pressure at 125°C (Kolbe–Schmitt reaction) to give B, which on acetylation with Ac_2O gives C. What is the major product C?

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EEJ MAIN Chemistry QUESTION #5582

Question 1

In a reaction sequence, sodium phenoxide reacts with $CO_2$ under pressure at 125°C (Kolbe–Schmitt reaction) to give B, which on acetylation with $Ac_2O$ gives C. What is the major product C?

Methyl salicylate (OH and $COOCH_3$ on ring)
Ortho-acetoxybenzoic acid ($OCOCH_3$ and $COOH$ ortho)✔️
Para-acetoxybenzoic acid ($OCOCH_3$ and $COOH$ para)
A compound with keto groups

Correct Answer Explanation

Kolbe–Schmitt reaction: Sodium phenoxide + $CO_2$ (125°C, 5 atm) → Sodium salicylate (2-hydroxybenzoate), acidified to give salicylic acid (B = 2-hydroxybenzoic acid). Acetylation of salicylic acid with $Ac_2O$ preferentially acetylates the –OH group → product C = 2-(acetyloxy)benzoic acid = aspirin (ortho-acetoxybenzoic acid).

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