Hi! :)
As always, the wheels just keep on turning inside this bee's head, and Ive started to wonder, with all this talk of 2,3,4,5-Bis-MD-P2P syntheses, Ive wondered about the 2,3,5,6-Bis-MD-P2P version. Its symmetrical and thus better :P
Jokes aside, I wonder if this is a possible route to such a compound? Although long, can you think of other routes to such compound that dont involve the destruction of premade substitutions on the aromatic ring? I think that is so rude, to rip off the creations of nature, and replace them with your own. Stealers! :P
Toluene = PhMe
PhMe + HNO3 ==H2SO4==> para-NO2PhMe (nitrotoluene)
para-NO2PhMe + Al ==H2SO4==> 2,5-dihydroxy-1-methylbenzene
As shown here:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/quinones.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/quinones.html)
Look under # 3.
2,5-dihydroxy-1-methylbenzene + Calcium hypochlorite --> 2,5-dihydroxy-1-(dichloromethyl)benzene ==KOH==> 2,5-dihydroxy-benzaldehyde ==NaOH, H2O2, Dakin Reaction==> 1,2,4-trihydroxybenzene
1,2,4-trihydroxybenzene + vinyl chloride --> 2-vinyloxy-benzene-1,4-diol --HEAT--> 5-vinyl-benzene-1,2,4-triol --KMnO4--> 2,4,5-trihydroxy-benzaldehyde --Dakin reaction--> Benzene-1,2,4,5-tetraol
Benzene-1,2,4,5-tetraol + DCM ==PTC==> 1,2,4,5-Bis-Methylenedioxy-Benzene
1,2,4,5-Bis-MD-Benzene + Mn(OOCCH3)3 ==AcOH==> 2,3,5,6-Bis-MD-P2P
Hmm, I can already see a few problems with this, but it was still fun to write! Any comments, maybe some better ideas?
PrimoPyro
Vivent Longtemps la Ruche! STRIKE For President!
Post 245368 (https://www.thevespiary.org/talk/index.php?topic=7025.msg24536800#msg24536800)
(Rhodium: "Any known bis-methylenedioxy compounds?", Chemistry Discourse)
enclose the post in square parenthesis Post 246184 (https://www.thevespiary.org/talk/index.php?topic=7025.msg24618400#msg24618400)
(boppesz: "Re: Any known "bis-methylenedioxy" compounds?", Chemistry Discourse)