Hydroquinone

[dildoque]

Is there a simple way from 2-alkyl-phenol to 2-alkyl-1,4-dihydroxybenzene ? NO2->NH2->OH or Br->OH

[Rhodium]

Both are possibilities, but I would think that the latter alternative would be better. The first one will produce a lot of o-nitrated phenol. Use a bulky brominating agent, and the para-selectivity will be good. Then reflux the bromide with Cu powder in a KOH solution to get the hydroquinone.

Another method would be to formylate the phenol in the para position, and then oxidize the aldehyde to the phenol using bayer-villiger conditions.

http://rhodium.lycaeum.org