4−Amino salicylic acid, called PAS, is an anti-tuberculosis drug. The proper method for its preparation involves a reaction of:
A
3−aminophenol with chloroform in an alkaline medium
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B
3−aminophenol 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 4−aminobenzoic acid in the pressure of FeCl3, followed by boiling the product in aq. alkali
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Solution
The correct option is C3−aminophenol 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.