Terephthalic acid: spot the regiochemistry flaw

Single question

Two-step route to terephthalic acid: dimethylate benzene to a xylene, then oxidize both methyls to carboxylic acids with Co/Mn/Br in HOAc. Check the regiochemistry of the dimethylated intermediate.

Methyl directing effects in Friedel-Crafts

Selectivity for p-xylene over m-xylene

Why m-xylene oxidation gives isophthalic acid, not terephthalic

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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