(Hive Bee)
09-18-02 16:15
No 357660
(Rated as: excellent)
This is one of the 'Wanted references':
Synthesis of 1-(4-hydroxy-3-methoxyphenyl)-2-propanon
Nippon Kagaku Kaishi 1972, (8), 1540-1
Unfortunately it's in Japanese (job for translator Smith ?) but there's enough info to get a good idea of what it's about.
Mountain Boy
(Hive Bee)
09-18-02 16:19
No 357663
Now I'm wondering, even if yields of around 30% are acceptable, exactly how do you turn the ketone into something useful ?
Mountain Boy
(Hive Bee)
09-19-02 14:04
No 358077
"Now I'm wondering, even if yields of around 30% are acceptable, exactly how do you turn the ketone into something useful ?"
1. Brominate the 5 position
2. Convert to 3-meo-4,5-hydroxy phenylacetone with Cu or CuBr
3. Methylate with DMS or MeI to 3,4,5-trimethoxy phenylacetone
[cf. mescaline from vanillin @ Rhodium's]
The paper seems to suggest that the PdCl2 is regenerated. If it can be mostly recovered, maybe something can be done with that liter of Eugenol that has been sulking in the corner, waiting to be 'picked' instead of being ignored for her prettier sister Safrole ('That slut!')...
Mountain Boy
(Stoni's sexual toy)
09-19-02 15:10
No 358086
> The paper seems to suggest that the PdCl2 is regenerated.
In theory it should be. But looking at their yields and the amounts of CuCl2 employed makes me believe not much catalyst regeneration is taking place. This procedure definitely needs some additional work.
> 1. Brominate the 5 position
> 2. Convert to 3-meo-4,5-hydroxy phenylacetone with Cu or CuBr
> 3. Methylate with DMS or MeI to 3,4,5-trimethoxy phenylacetone
> [cf. mescaline from vanillin @ Rhodium's]
Let me suggest the following procedure:
1. Perform this reaction in an alcoholic solvent (MeOH, EtOH, or ethandiol)
2. Isolate the ketal, since it is more stable in the following reactions
3. Convert to the diphenol, or better yet syringylketone
4. alkylate the 4 position (lots of interesting possibilities)
Maybe stuff like 3-MeO-4-allylamphetamine or 3-MeO-4-EtO-amphetamine will be a worthwhile target for some, so let's not forget about these potentially interesting compounds.
I'm not fat just horizontally disproportionate.
(Hive Bee)
09-23-02 02:35
No 359275
Ethoxylate the 4-hydroxy of eugenol (eu = good, ol = alcohol) with either CH3CH2I or NaOEt and anhydrous pure grain alcohol I think or friends (diethylsulfate) to obtain 4-EtO-3-MeO-allylbenzene.
Forget brominating the 5 position. If you want TMA, use elemi oil.
Forget the copper catalyst and used PdCl2 and benzoquinone in either DMF or a much cheaper alcohol to get the the propanone (search engine keyword: ghetto reactor I think). Some O2 pressure may help this reaction's kinetics.
I really don't know.
Reduce with Heavy Duty Reynold's Aluminum foil, nitromethane (keyword: MaDMAx) and not a lot of HgCl2 to get 4-Ethoxy-3-Methoxy-methamphetamine (Miss EMMA). I believe eugenol may be found in Magnolia flowers: smells like it anyway.
If you prefer, methoxylate #4 with CH3I (or was it NaOMe?) and MeOH or dimethylsulfate to get 3,4-dimethoxymethamphetamine (MMMA or Andre 3000 because M = 1000 in Roman numerals).
If you'd rather, mix the propanone with NH2COH (formamide)and hydrolyze with lye and heat (reflux it at the proper temperature for the proper length of time; look them up first) to get either 4-EtO-3-MeO-amphetamine (EMA) or 3-MeO-4-MeO-amphetamine (MMA or Andre 2000).
Position numero 4 can also be n-propylated or
n-isopropylated, but that's another chapter.
Enjoy!
(Hive Bee)
09-23-02 08:56
No 359405
Neuro:
4-Ethoxy-3-Methoxy-methamphetamine - any idea of the activity of this compound ? From what Shulgin says the PEA derivative (PIHKAL #123) has low activity.
I recall reading somewhere that Magnolia contains 4-methoxy eugenol (a.k.a. methyl eugenol).
Regarding 3,4-dimethoxy amphetamine, Shulgin says (PIHKAL #55) it's not active, at least in reasonable doses. I expect the methamphetamine would be even less potent.
Allylation like Os says is probably a better way to go.
Right now eugenol is still an ugly duckling but will one day be quite a desirable babe
Mountain Boy
09-23-02 18:11
(Rated as: insignificant)