Benzene first reacts with the reagents CHX3Cl/AlClX3, to attach a methyl (CHX3) group to the benzene ring.
Then I suggested reacting with OHX−. Because the methyl group is an activator, it will cause the OHX− electrophile to attack either in the para or ortho positions. In this case I suggest it will attack the ortho position. Now we have two activators, hydroxyl and methyl, but because hydroxyl is a stronger activator, the position where the next molecule attacks will be controlled by the hydroxyl group.
The next electrophile that attacks is the NOX2X+, through the reaction HNOX3/HX2SOX4, the nitro group will attack the para position of the benzene and we get our final product 2-methyl-4-nitrophenol.
However, I am not 100% sure if the methyl group should be introduced first to form toluene or the hydroxyl group to form a phenol.
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