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Yeah, I know I could reduce the benzaldehyde...

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phenethyl_man:
Yeah, I know I could reduce the benzaldehyde but then I have to reformylate etc, and as you know I would rather just use this for other materials.

I tried that reduction of p-nitrotoluene with aluminum.  Yields are low and my residence got fumigated with toxic fumes so that route was abandoned.  The patent is very vague, do you know the reaction mechanism here?  I have a feeling it releases some not so friendly gases; at least with the aluminum foil I used.  The o-toluidine route seems like too much work; at least from toluene.  Nitration of toluene will give a mixture of ortho/para-nitrotoluene which would then have to be reduced, then subjected to those two reactions to finally arrive at toluhydroquinone (which I can just purchase anyway).

Basically, I have a bunch of hydroquinone and p-dimethoxybenzene lying around and want some 2,5-dimethoxytoluene.  :)

Formylation, reduction, and reformylation seems quite tedious.

I just don't see why Friedel-Crafts alkylation won't work.  And I don't understand why Shulgin uses a low-yielding acylation followed by reduction (PiHKAL: DOET, DOPR) to arrive at his alkylbenzenes when this seems feasible for a high yield of any alkylbenzene in just one rxn.

Saddam_Hussein:
It is also possible to reduce the -CHO of 2-hydroxy-5-methoxybenzaldehyde, a rather OTC substance (if you want). You can (m)ethylate and have a nice DOM precursor as well  :) . I used to have a procedure involving ethyl chloroformate doing the trick, but my pile of junk is rather immense.

hest:
Acetylation yeald a deactivated product, alkylatein an activated one. So the risk for more than one acetylation on the rin is low. The risk for more than one alkylation on the ring is high.
The Lewis accid used in the alkylation might cleawe the methoxyethers.
PErsonal I prefere bromination and the BuLi and RBr

phenethyl_man:
The Lewis accid used in the alkylation might cleawe the methoxyethers.
--- End quote ---


the Friedel-Crafts alkylation w/alcohols doesn't require a lewis acid..  I doubt AlCl3 would cleave the ethers anyhow as long as the solvent is right, otherwise bees wouldn't be having so many problems cleaving eugenol/vanillin's methoxy groups.

PErsonal I prefere bromination and the BuLi and RBr
--- End quote ---


you must like performing reactions at -70degC under an inert atmosphere and anhydrous conditions, eh?  not to mention the hassle obtaining butyllithium.


Saddam_Hussein - excuse my ignorance, but by what means is this aldehyde "OTC"?

Captain_America:
Saddam_Hussein - excuse my ignorance, but by what means is this aldehyde "OTC"?

It meens you can make it from OTC chemicals;

Post 530676 (Captain_America: "OTC 2C-H", Methods Discourse)

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