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Chemi Pharma
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I think the attachment will be very useful for those who intends to demethylate vanilin or iso-eugenol and want to close the benzodioxile ring later
to produce piperonal and safrole.
Two methods to demethylation and two methods to close the benzodioxile ring are given.
Attachment: amphetamine.rar (2.4MB)
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RosarioHeis
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Something you may want to try as far as you can get some aromatic solvent
http://chemistry.mdma.ch/hiveboard/novel/000291912.html
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Rhodanide
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Quote: Originally posted by chemplayer..  |
That said, don't be discouraged as vanillin itself is easily available, very interesting and you can do a lot of great experiments with it
(condensations, benzylidene compounds, nucleophilic substitution on the carbonyl, electrophilic substitution etc.). |
Hey, did you ever get to successfully make Vanillin nitrile/cyanide?
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chemplayer...
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No unfortunately not - all attempts failed but we think that nickel boride may be a workable path to vanillylamine from the oxime.
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byko3y
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Vanillin nitrile would be a relatively unstable compound dure to the fact it's slightly acidic by itself, and reacts with itself in acidic conditions
( https://en.wikipedia.org/wiki/Hoesch_reaction ). I'd suggest to protect hydroxy group first.
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clearly_not_atara
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Doesn't Zn/NiCl2 reduce oximes? There is a patent saying so:
http://www.sciencemadness.org/talk/viewthread.php?tid=20153#...
Although in this case it seems that Zn/NiCl2 reduction of the imine would suffice.
However I think the most efficient route would be the Mannich reaction of formaldehyde and ammonia with guaiacol, would it not?
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Cryolite.
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I always thought the Mannich was a little dodgy with primary amines and ammonia, since the resulting primary/secondary amine forms a more stable imine
leading to overalkylation.
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byko3y
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clearly_not_atara, it's called a Duff formylation. I'm not sure whether it's possible to stop the reaction at amine stage. Also ortho-to-hydroxy
substitution product might be a major one instead of para.
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