Author Topic: m-methoxyphenylacetic acid-------->  (Read 3427 times)

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Rhodium

  • Guest
If you start with common ortho-cresol ...
« Reply #20 on: July 19, 2002, 09:41:00 PM »
If you start with common ortho-cresol (o-Me-Phenol), you methylate the phenol, and either make the benzaldehyde or benzyl chloride through any common route, and from there proceed either via the nitrostyrene or benzyl cyanide to the PEA...

...or oxidize the methyl to the acid and then to the alcohol and then as above either via benzyl halide or benzaldehyde.

The funny part is that common aspirin also is a good precursor :)

Dr_Heckyll

  • Guest
This is the beginning...
« Reply #21 on: July 20, 2002, 04:04:00 AM »
On July 17, 2002, at 22:26, a stranger nicknamed Dr. Heckyll started the revolution with a carefully launched post:
the love drugs wave was borne.

Make love not war becomes a reality.

And this is only the beginning. The good Dr. Heckyll has more on store, so much more. Just be patient...

{Make sure you notice that the post is marked with a  ;) }




Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.

Chemikaze

  • Guest
aspirin
« Reply #22 on: July 20, 2002, 02:46:00 PM »
And what do you suggest we should do to aspirin to make it o-meo... etc.?

When I die bury me upside down so the world can kiss my ass.

Rhodium

  • Guest
Hydrolyse the acetyl ester with aqueous base, ...
« Reply #23 on: July 20, 2002, 02:49:00 PM »
Hydrolyse the acetyl ester with aqueous base, yielding o-hydroxy-benzoic acid. Reduce the acid to the alcohol, methylate the phenol, and then make either the benzaldehyde or the benzyl halide from the o-methoxy-benzylalcohol.

PrimoPyro

  • Guest
Aromatic Nitroso groups
« Reply #24 on: July 20, 2002, 03:05:00 PM »
Can one react an aromatic nitroso group (Ar-N=O) With hydroxylamine and HCl to form a diazonium salt?

Ar-N=O + H2N-OH --> Ar-N=N-OH + H2O
Ar-N=N-OH + HCl --> Ar-N#N+Cl- (ionic salt) (# = triple bond)

This could prove useful on a larger scale manufacture of your ortho-methoxyphenylalkyl derivatives, by utilizing the following series:

Baudisch Reaction:



Followed by methylation of the free phenol form, then diazotization of the nitroso via the method proposed above.

The final step would be conversion of the phenyl-diazonium salt to the benzaldehyde via the method in

Post 322750

(Tricky: "Benzaldehydes from diazonium salt, OTC!", Novel Discourse)
which is supplemented by information in OrgSyn.

Benzene --> o-(OH)(NO)PhH --> o-(OMe)(NO)PhH --> o-(OMe)(NNCl)PhH --> o-(OMe)(CHO)PhH

And from the benzaldehyde its all familiar territory for the rest of the syntheses.

                                                  PrimoPyro

PrimoPyro

  • Guest
On Second Thought
« Reply #25 on: July 20, 2002, 03:10:00 PM »
Hahahaha, forget all that crap. I totally misses the obvious:

Phenol + reimer-tiemann + DMS methylation. Man, thats a lot simpler.

Phenol is cheap, CHCl3 is cheap, KOH is cheap. DMS can be made from cheap MeOH and H2SO4. Cheap cheap cheap! A lot cheaper and easier than the prior post of mine.

Yeah the reimer tiemann yield isnt so hot from phenol, and some of it will be the wrong isomer, but the ingedients are so cheap, easy to get, and its such an easy reaction, that one shouldnt be stopped by this imperfection. Just my opinion.

                                                  PrimoPyro

Dr_Heckyll

  • Guest
Cheap
« Reply #26 on: July 20, 2002, 05:23:00 PM »
When calculating the cost, you'll have to consider the effort to clean up the aldehyde and subsequent intermediates till you arrive at the o-methoxybenzaldehyde. Even an optimized Reimer-Tiemann (

Patent US4755613

) yields only about 77% of the desired isomer. The p-isomer can be extracted with Et2O. How laborious is the methylation and the clean-up?

How compares that to a price of ~$450 for 2.5 kg of o-methoxybenzaldehyde? Assuming an all-over by-weight yield of 50% based on the o-methoxybenzaldehyde, and a dose of 10 mg of o-methoxyphenylethylamine, this is only $0.0036 for the o-methoxybenzaldehyde per dose, which in my opinion is insignificant.



Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.

Chemikaze

  • Guest
reducing acid
« Reply #27 on: July 20, 2002, 08:10:00 PM »
Rhodium: How would we reduce acid to alcohol...EDIT:oops? ::)

When I die bury me upside down so the world can kiss my ass.

Rhodium

  • Guest
LAH, Na/EtOH, NaBH4/I2, NaBH4/H2SO4 etc...
« Reply #28 on: July 20, 2002, 08:20:00 PM »
LAH, Na/EtOH, NaBH4/I2, NaBH4/H2SO4 etc...

toad

  • Guest
2-methoxy-phenethylamine *dud*
« Reply #29 on: August 05, 2002, 11:46:00 PM »
Hiyall,

2-methoxy-phenethylamine = *dud*

sorry to burst the bubble but i saw this exciting patent
a couple of years ago and forged ahead with the 2-methoxy-pea.
was even so fortunate to find that it's available commercially!
unfortunatly its effects were
nothing like described in the patent (for myself [male] and
also a female experimentor friend). If I recall correctly we
Worked it up to 75-100mg in a single dose and also tried 5-10mg
several times a day as described in the patent. I have
since lost my notes on this subject so I must resort to
memory with regards to the activity or lack there of. 
There was definitely something going on but not sexually
stimulating, mentally stimulating, or otherwise interesting
to this experienced lab rat.  no idea about the other subs,
we chose not to pursue them due to the lack
of positive results with 2-meo and the fact that
that we would have to spend a lot of time/effort/money
to synth the 3-meo ourselves. We ended up throwing all
the remaining 2-meo material away...
 
yet another case of wishful patenting... or perhaps
the other subs are better than the 2-meo???
seems there are *a lot* of patents like this, where
the baby just doesn't live up to it's billing.

hope this saves a few bees some valuable time/effort/money.

keep digging and dreaming !

cheers,

Toadie

master of the alchemikal arts

Dr_Heckyll

  • Guest
Patents
« Reply #30 on: August 06, 2002, 04:30:00 AM »
Just because something is patented doesn't mean it's real and working! One of my "favourite" patents is a way of treating tumors by irradiating its antimatter. In practice, they put a mirror next to the patient in about 1 m distance. Then they irradiate with some hard radiation the virtual mirror image of the tumor, i.e. a point about 1 m behind the mirror, some 2 m away from the actual tumor, where they claim is the antimatter part of the tumor, and by destroying it's antimatter, the patient gets cured...  ::) . (I'm citing from memory; if you're curious, just search patents for "antimatter", there isn't much popping up, and one of the few is it  ;D .)

So no, a patents doesn't guarantee the validity of a technology. But a reputable company, let's say Merck & Co., is less likely than individual inventors or small companies/institutes to patent some weird dreams.



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