Nitration of Hydroquinone

[A.Scriabin]

I've obtained 100g of hidroquinone (para-idroxyphenol), and I'm curious about the products of a possible nitration, and the properties of the compounds. Because the starting material has 2 activating groups, the nitration shouldn't be difficult...did someone tried this experience?in the licterature I never seen a "trinitro-idroxyphenol " etc..:eek:

[Chris The Great]

Most likely scenario is that the nitric acid oxidizes the hydroquinone and starts a runaway reaction. The stuff is very easily oxidized and the quinone doesn't look like something that would survive in a nitrating acid mixture.

If it did not oxidize, then you'd probably get the dinitro compound, 2,5-dinitro-1,4-dihydroxybenzene.

[FUTI]

A.Scriabin you had started a good subject. I like chemistry of quinones which is inseparable from hydroquinones. Product of nitration of quinone (IIRC) is 2,5-dinitro-3-hydroxy-1,4-benzoquinone (yes it inserts extra hydroxy group don't ask me how), but I could be wrong (anyway it should depend on conditions and reagents used for nitration). That product is naturally explosive like many nitrated compound is. If you can find a book by Saul Patai "Chemistry of Quinonoid compounds" you can find an full answer there (my info is from Houben-Weyl "Methoden der Organischen Chemie" I think). And if you find Patai's book grab it and please scan it. I look for it more then I remember. We could both benefit from that book - you would find a conditions for non-runaway-nitration of hydroquinone, and I would find a long lost treasure I'm seeking.