conducter - 3-2-2007 at 17:36
On rhodiums archive there is a synthesis from
Eugenol -> Isoeugenol -> MethylVanillylKetone
What the hell is methylvanillylketone, what compound is it?
Ive googled it and there is no info on it.
pantone159 - 3-2-2007 at 18:35
Vanillin is 4-hydroxy-3-methoxy-benzaldehyde, i.e.,
3-OMe,4-OH-Ph-C(=O)-H
so I'd (now) guess (not positive) that 'methyl vanillyl ketone' is
3-OMe,4-OH-Ph-CH2-C(=O)-Me
EDIT: Corrected formula to the more likely 3-carbon chain.
[Edited on 4-2-2007 by pantone159]
Sauron - 3-2-2007 at 21:17
It's crappy nomenclature. My guess is (considering the source) that the final compound was not a substituted acetophenone, but rather a substituted
benzyl methyl ketone, i.e., a substituted P2P, an amphetamine precursor.
Anytime anyone on the Hive starts talking vanillin or safrole, that is what they have on their mind.
conducter - 3-2-2007 at 21:56
that is what i thought Sauron, it couldnt be MDP2P could it?
I believe MDP2P is called Methyl Piperonyl Ketone but Methyl Vanillyl Ketone is very close sounding.
pantone159 - 3-2-2007 at 22:32
MDP2P has the 3-4 positions connected by a R3-O-CH2-O-R4 ring, where R3 is the 3 position and R4 the 4 position of the benzene ring.
Vanillin has the 3 and 4 substitutions as separate groups, not connected, so they aren't the same. If you could somehow fuse the 3,4 groups into a
methylenedioxy ring, then you WOULD have MDP2P, however.
[Edited on 4-2-2007 by pantone159]
Sauron - 3-2-2007 at 22:58
@Pantone is perfectly correct. And "methyl piperonyl ketone" is just as objectionable as nomenclature, as "methyl vanillyl ketone" All P2P's are
phenyl-2-propanones regardless of ring substituents, that is methyl BENZYL ketone or phenylacetone.
So methyl 3,4-methylenedioxybenzyl ketone would be correct for "MDP2P" for example but methyl piperonyl ketone just does not convey all the
information required.
Which is how we get posters like the one a couple weeks ago who didn't know the difference between acetophenone and P2P. The fellow who thought you
could just oxidize methyl phenyl carbinol to P2P.
Reference Information
solo - 4-2-2007 at 12:08
I was able to find a reference to that name in this patent.....
Method of preparing optically active L-alpha-methyl 3,4-dihydroxy phenylalanine. Patent US03366679.....Example 11
........here is the whole patent,
[Edited on 4-2-2007 by solo]
Attachment: method of preparing optically active L-alpha-methyl 3,4-dihydroxy phenylalanine. US03366679 patent.pdf (1.1MB)
This file has been downloaded 806 times
unionised - 4-2-2007 at 12:13
Is this nomenclature "methyl phenyl carbinol " any better than methyl phenyl ketone?
Sauron - 4-2-2007 at 12:51
IUPAC would not approve. But it's a good old system.
@solo, that's some travesty committed by a patent lawyer. He should be obliged to east his Martindale Hubble without margarine.
[Edited on 4-2-2007 by Sauron]
Nicodem - 5-2-2007 at 13:15
Actually IUPAC does condone exceptional use of such names for the ketones describing the substituents around the carbonyl (like phenyl methyl ketone,
for example). Mind that this is not really a IUPAC nomenclature, it is just tolerated to some degree, kind of like old trivial names are tolerated
(acetophenone, for example). But going so far as trying to use the archaic name of carbinol for methanol and using faulty nomenclature as 'phenyl
methyl carbinol' is a dreadful crime in the view of IUPAC puritans. But still one sees this name in the scientific literature even nowadays. Old
habits die hard.