Byzantine Route To 2,3,5,6-Bis-MD-P2P

[PrimoPyro]

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  

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!  

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

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!

[hest]

Post 245368

(Rhodium: "Any known bis-methylenedioxy compounds?", Chemistry Discourse)

[PrimoPyro]

Thats definitely a better way to make it than this. I cant wait for your results hest on the oxidation of hydroquinone.

I thought that thread was on the 2,3,4,5-MD derivative. Damn.

                                                PrimoPyro
Vivent Longtemps la Ruche!

[amalgum]

Shit I just like that method to the 2,5 substitution scheme, easy way to make 2C-B or maybe DOB from toluene.....

[hest]

P.P. Talk with the boos abuth that  

[boppesz]

What about this : Post No 246184 ?

How do I fix this link?

[bujinkan]

enclose the post in square parenthesis

Post 246184

(boppesz: "Re: Any known "bis-methylenedioxy" compounds?", Chemistry Discourse)

[PrimoPyro]

boppesz:    Yum Yum  
Vivent Longtemps la Ruche!

[boppesz]

Did you mean this sarcastic? I know that we can't make a symetrical allylbenzene out of dillapiole, but we can make [2,3][4,5]bismethylenedioxyallylbenzene. If we want to, but of course we don't perform criminal activities.....

[Aurelius]

does somebody have the pharmacology info for this comp?

[Rhodium]

Definitely not, it hasn't been prepared by anyone yet.

[boppesz]

I devenitely give it a try when I get dillapiole. But that will take a while because I have to experiment first with the ordinary procedures to get them allright. So maybe I'll not be the most right person to do that, untill you guys like to wait for a year