JEE Advanced levelSingle correct optionDifficulty 3 of 3ap126
4-Methylphenol is heated with CHClX3 and aqueous NaOH, and then acidified. Considering only the normal Reimer-Tiemann product (formyl group on the ring), the major product is
A4-hydroxy-3-methylbenzaldehyde
B2-hydroxy-5-methylbenzaldehyde
C2-hydroxy-3-methylbenzaldehyde
D4-methylbenzaldehyde
Answer: B
The para position is blocked by the methyl group, so dichlorocarbene attacks an ortho position of the phenoxide. This puts −CHO on C-2 relative to −OH at C-1; numbering from the aldehyde carbon (C-1) gives −OH at C-2 and −CHX3 at C-5.