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Question

4−Amino salicylic acid, called PAS, is an anti-tuberculosis drug. The proper method for its preparation involves a reaction of:

A
3aminophenol with chloroform in an alkaline medium
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B
3aminophenol with carbon dioxide in an alkaline medium under pressure
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C
conc.HNO3 and conc.H2SO4 on salicylic acid followed by catalytic reduction using H2/Ni
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D
chlorine (limited amount) with 4aminobenzoic acid in the pressure of FeCl3, followed by boiling the product in aq. alkali
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Solution

The correct option is C 3aminophenol with carbon dioxide in an alkaline medium under pressure
The reaction is known as Kolbe's reaction.
Phenolic OH reacts with NaOH/KOH to form phenoxide ion which is more reactive than parent phenol towards electrophilic aromatic substitution. Carbon dioxide is weak electrophile. Both OH and NH2 groups are ortho, para directing groups.
821171_884976_ans_0f1127b1bdd3479c9380702b9538d74e.png

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