well.. SWIM gave in and just ordered some more THQ anyhow, but here's a few more ideas for those interested:
starting from phenol:
ortho-methylate phenol with formaldehyde and base as described in
Patent US2401608
to obtain o-cresol; briefly discussed in this
Post 505367
(psyloxy: "H2O2 o-cresol to 2,5-dihydroxytoluene, 98%", Methods Discourse)Patent IE904369
describes the preparation of toluhydroquinone from o-cresol. o-cresol is acetylated (the patent states that even plain old acetic acid will work, though the examples only use acetyl chloride) to 4'-hydroxy-3'-methyl-acetophenone catalysed by HF. The acetophenone is then oxidised to toluhydroquinone via alkaline H2O2.
I'm not familiar with the manipulation of acetophenone's to obtain phenylisopropylamines, but perhaps it would be a good idea to try methylating this, the target compound then being 4-methoxy-3-methylamphetamine. Note this is like an iso-MMA, the substituents being reversed. The combination of an alkyl (C1-C3) or halogen in the 3 or 4 positions, combined with at least one methoxyl group somewhere else on the ring seems to almost always lead to activity, probably a little lower than MMA in potency I would guess?
Back to STP; I'm somewhat confused here. Wouldn't a simple oxidation of o-cresol with alkaline persulfate (elbs rxn) directly give toluhydroquinone.. or would the methyl group get oxidised?
I'm also wondering if that ortho-alkylation of phenols could be applied directly to hydroquinone to get toluhydroquinone, and if paraformaldehyde could be used in this process or if depolymerization or the use of formalin as in the patent would be necessary..
any thoughts?