BobHawson - 26-2-2009 at 20:48
How would one convert acetominophen to aniline?
not_important - 26-2-2009 at 22:54
Trade it with someone who has both aniline and a headache.
It is difficult to get the HO- off of benzene rings, requiring forcing conditions or expensive reagents, and giving low yields.
If you're that desperate for aniline, consider getting benzoic acid - say making it from toluene or polystyrene - and then
1) decarboxylate that to benzene, nitrate it, then reduce to aniline.
or
2) convert to benzamide, then use the Hoffman rearrangement/degradation to convert that to aniline.
smuv - 27-2-2009 at 05:13
Hoffmann degradation of benzamide works pretty well, there is a thread about this; just make sure you keep solution as cold as possible while you are
making the N-Chloramide.
You might want to consider p-aminobenzoic acid (PABA) to aniline; it might be activated enough that an acid catalyzed decarboxylation would work out.
Acid catalyzed decarboxylations are covered in March's advanced organic chemistry, check it out.
Picric-A - 27-2-2009 at 06:39
OH- groups can be removed (i know in the case of phenol) by passing the substance over heated Zinc powder, the product being zinc oxide and hydrogen.
Whether this will work in the case of parcetamol i am not sure but i see no reason why not.
not_important - 27-2-2009 at 08:41
The zinc reaction fits forcing conditions and low yields, it was more of an analytical tool to help establish structure back in the days of Queen
Vicky.