Starting with benzene, I need to obtain 2-nitro-4-chlorophenol using nitration, chlorination, sulfonation and hydroxylation in the correct orders, written question, not a lab procedure.
I've come up with this and I'm just wondering if it's the most efficient way:
1. Chlorination, since chlorine is an ortho-para director
2. sulfonation/hydroxylation to add the OH group in the para position, OH is an ortho-para director
3. nitration, adding the NO2 group in the ortho position