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Anise oil as PMA precursor

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senzualus:
I've read some reference about cleavege of the methoxy group here on the hive (it was somthing about eugenol I think...?)
It was a method involving AlCl3 I guess...

I'll get back to you on that...

GC_MS:
You can convert anethole to anol using several methods, but they usually give low yields. I'm not sure AlCl3 (or AlI3) will work for anethole, since I'm affraid a Friedel-Crafts polymerization reaction might kick in.
However, conversion of p-methoxybenzaldehyde to p-hydroxybenzaldehyde is feasible if you have aluminium foil and I2 crystals (AlI3 is a very good ether cleavage Lewis acid; e.g. Post 422757 (GC_MS: "Aluminium iodide in ether cleavage", Methods Discourse)). In a pure theoretical way, p-hydroxybenzaldehyde is a gateway toward two classes of goodies:
1. by monobromination of p-hydroxybenzaldehyde, 3-bromo-4-hydroxybenzaldehyde is obtained. What happens if the bromo group is substituted for hydroxy? Yup, correct. But I don't understand why one would try this alternative though. Vanilline is much easier and requires less hazardous chemicals (like the bromine).
2. by dibromination of p-hydroxybenzaldehyde, a precursor for 3,4,5-trimethoxy and triethoxybenzaldehyde is obtained. p-Methoxybenzaldehyde can be dibrominated as well, wich might be an interesting precursor for EME.

All pure theoretically though.

senzualus:
about the use of lewis acids to cleave aryl methoxy groups...

I haven't tried it (and I don't know if anyone has) but maybe someday...

https://www.thevespiary.org/rhodium/Rhodium/chemistry/eugenol.mdma.html

GC_MS:
I remember subjecting anise oil to a bromination reaction and had a yellow oil as result.

hypo:
> ~100% anise was brominated.

how do you know?
weight increase? tlc? boiling point?

(can you try with KBr?)

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