Basicly i want to know if there is a way to remove the 3,4 Methelenedioxy from the dmmda molocule. Leaving 2,5DMA just a short bromination step from DOB. Possibly this must be done before amination if nescesary.  Convert the aipole into 2,5 dimethoxyallybenzene.  Isomerize.  then either nitrosaturate to make the nitropropene,  do a wacker on the ally benzene, or try a peracid epoxidation.  All followed by the regular reduction routes to the amine.??
VL_

You cannot tear a methylenedioxy ring off the molecule without destroying the entire benzene ring. I am sorry.

                                                   PrimoPyro

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Vivent Longtemps La Ruche!

Would it be possible then to remove the O from the 4methoxy on asarone yeilding 4methyl-2,5dimethoxy suitable for DOM production?  or possibly selectivly cleave the whole 4 methoxy to leave 2,5dimethoxy?  what are the conditions for selective cleaving.  Perhaps a haphazard attempt could be made to destroy the methoxy with acid then seperate via fractional distillation.  Mabye VL_needs to sleep.

No, that's impossible. Sorry

Antoncho

P.S. Isn't it true that DOB sucks by all means? From the data i gathered from Russian sources, it does.

Dob is awesom.  DOM was the desired amine though.
Vl_

Yes, DOB is really great, with the exception of the very long "tail" of stimulation.

With the exception of the very long "tail" of stimulation.  in swims experience the tail of stimulation was plesent and filled with visuals.  I remember getting home from a club while we had some dob and the spotts on the leperd skin bed cover each flowed independant of each other in each it own unique pattern.  it was amazing.  I could charchterize it as a cornocoupia of visuals followed by some minor depersonalization. No real body load to speak of.  the club was so visualistic that i thought i wasn't tripping......  then i walked outside..Oh my god.. can you go from thinking that youre sober one minute then walking outside and having the desert horizon look like an ocean flowing with waves and all  with the sun coming over the horizon at 4oclock in the morning.  yes the sun does come up at four there. 
someone needs to flood the planet with that great substance.
VL_

Thank you very much for the positive input, guys! I appreciate it.

Antoncho

> Would it be possible then to remove the O from the
> 4methoxy on asarone yeilding 4methyl-2,5dimethoxy
> suitable for DOM production?  or possibly selectivly
> cleave the whole 4 methoxy to leave 2,5dimethoxy?

There is an obscure old ref from 1937 by some Indian researchers who claim that selenium dioxide converts asarone to 2,5-dimethoxypropenylbenzene. I have no idea how that is supposed to happen and I haven't seen any other refs detailing such a reaction, so I'm not sure if this really works or not.

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I'm not fat just horizontally disproportionate.

Os if you can find the time to dig up that ref or point in the right direction VL_ has a friend who is dying to try it.
VL_

Ah - hello fellow bees!  After a long hiatus, I'm back   .

This post caught my eye, and I found the reference:
JCS (1937) p.1338  ß-Asarone, Rao & Subramaniam

excerpt:
(a) Action of Selenium Dioxide on ß-Asarone - A mixture of ß-asarone (70 g) alcohol (100 ml) and selenium dioxide (10 g) was heated on the water-bath for ½ hour.  The filtered solution was poured into water, the oil dissolved in ether, and the dried etheral extract evaporated; the residue partly crystallized, and distillation gave asarone (60 g).

(b) A mixture of ß-asarone (20g), alcohol (50 ml) and selenium dioxide (5 g) was boiled for 5 hours.  The product isloated by ether in the usual manner gave an oil, which on distillation under 8 mm gave two fractions: (i) bp 140-145º, d30º/30º 1.052, n20º/d 1.5451; (ii) bp 145-150º.  From the former, a picrate was prepared, crystallizing from alcohol in orange-red feathery leaflets, mp 87º.  Decomposition of the picrate with alkali gave 2,5-dimethoxypropenylbenzene, bp 128-129º/4 mm., d30º/30º 1.041, n30º/d 1.5548.  The nitrosite, mp 118º, was a pale yellow powder.

What is the intermediate which is able to form a picrate?

I was wondering the same thing Rhodium.

And what is beta asarone? (Im sure Im the only one who doesnt know this one though.)

                                                   PrimoPyro

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Vivent Longtemps La Ruche!

What is the intermediate which is able to form a picrate?
Eh? They say that it was the picrate of 2,5-dimethoxypropenylbenzene.

And what is beta asarone?
The cis isomer. You really need to get yourself a Merck Index.

It is C₁₁H₁₄O₂,C₆H₃O₇N₃  This must be the picrate salt of 2,5-dimethoxypropenylbenzene.

The article also states:

Asarone     mp 62-63º  bp 167-168º/12 mm    nD_20º = 1.5683
ß-Asarone  mp  ----     bp 162-163º/12 mm    nD_20º = 1.5552

Yes you're right, but how come Im the only one here who get's chastized for asking questions like this? Everyone else just gets an answer, I get this, "You should do this, or do that" crap all the time from everyone.  

If I didn't have a sense of humor I'd call double standards.  

                                                    PrimoPyro

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Vivent Longtemps La Ruche!

PP: We know you can do better, and we know that you will have actual use of a Merck in the future. We are trying to help you become a professional by forcing you to aquire the literature you need - if you just get the small answers the others get, you will not grow as fast as you can  

Terbium: How could a propenylbenzene form a picrate salt?

> How could a propenylbenzene form a picrate salt?

It's not really a salt (as in M⁺X^-), but an addition compound/complex.
Picric acid can form solid derivatives with all kinds of substances (especially aromatics). In the older literature sometimes trinitrobenzene derivatives are mentioned, this is the same principle.

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I'm not fat just horizontally disproportionate.

IN excerpt (A)  the product is givin as Asarone.  Is that a typo.  And in excerpt B  there is two distillation fractions. do these correspond to the cis & trans isomers of the formed 2,5 Dimethoxypropenalbenzene.
Also is the picrite to be prepared by refluxing (powder)picric acid and rxn product in MeOh similar to forming an oxime but without base. What is the purpose of forming a picrite when it is just decomposed by the base.
Now that that is done with how might one add a Me to the 4 position.
VL_