Well not really...
i think, if the mechanism the authors suggest is correct (and it does make sense, IMHO), then it'll work for any
hydroquinone just fine.
But the alkylated species here is the hydroquinone, not the quinone, so i don't quite get the reasoning... maybee interesting 1st to reduce , then alkylate, then alkylate again using NaMeSO4 - i suppose, it doesn't alkylate amines, see what i'm aiming at?
The main point of my joy here - i feel the need to explain - is that p-methoxyphenol, and only p-methoxyphenol, is subject to Reimer-Tiemann formylation, and in good ~70% yield (tested by Karl) - which is very-very OTC, non-toxic - well, it's
kitchen chemistry at its best.
The alternative (starting w/p-diMeO-benzene, which SWIM has successfully made w/NaMeSO4) is Vilsmeier formylation, which requires smth like POCl3 (unaffordable for SWIM) or SOCl2 (can bee made from SCl2, but in a
VERY disgusting, stinky way). We'll just leave phosgene alone
The only previously known method of making p-methoxyphenol (BTW, also found by moi
- that's why i say 'part II') involved methylating HQ w/DMS in a two-phase system, whereas the formed product was continuously taken up in toluene, thus avoiding secondary methylation. Besides being non-OTC/toxic, that route still has ~20% of HQ converted to p-diMeObenzene.
An attempt to pull this rxn w/NaMeSO4 was made, but a major problem was encountered: toluene forms a low-boiling azeotrope w/water, and the temp. is insufficient for the NaMeSO4 methylation to effectively take place (although some product still has been isolated). SWIM was planning to try repeating it w/xylene, but w/out much hope, since bp of the azeotrope would bee lower than 100 C anyway.
Now having this procedure in hand... SWIM guesses it's time for him to start saving money for a bottle of chloroform, heh
Antoncho