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-the good reverend drone
Cherrie Baby
Member posted 04-20-99 01:08 AM
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How about sodium dichloroisocyanuarate (aka Baby feeding-bottle sterilizer)?
The last time I looked it up in a general synthetic methods catalog there was some indication that it could play an analogous role to that of bromosuccinic acid - for chloro-subst. rather than bromo-substitution.
Osmium
Member posted 04-20-99 04:18 AM
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A few months ago I posted a writeup of a vanillin bromination using KBr/H2SO4/H2O2. Another respected bee confirmed my results. Yields not quantitative but high (70-80 if I remember correctly).
Piglet
Member posted 04-20-99 12:44 PM
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I would think that syringl alcohol is more OTC since it's the major component of the esseential oil of syringl blossoms (or something 8). Can the aldehyde be simply derived from this.
Piglet
PS Have you reorganized your mail yet? Ay!
PPS I agree that escaline/proscaline look like very interesting compounds & last year I spent some time thinking about this problem...
rev drone
Member posted 04-20-99 02:00 PM
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Osmium,
The search engine isn't showing anything. Do you know the url of the posted results? What were the conditions?
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-the good reverend drone
Rhodium
Administrator posted 04-20-99 03:58 PM
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I can't find Osmium's original results either, so here are my own observations on the synthesis 5-Bromovanillin.
5.6 g KBr (50 mmol), 4.9 g 98% H2SO4 in 5 ml H2O (50 mmol) and 2.5 ml 35% H2O2
(25 mmol) was dissolved in 25 ml HOAc in a 100 ml RB flask equipped with magnetic
stirring. The solution was cooled below 10°C with an external ice-bath, and 7.6g
vanillin (50 mmol) in 25 ml HOAc was added dropwise through an addition funnel
to the orange solution during 15 minutes. Another 2.5 ml 35% H2O2 (25 mmol) was
added in five portions with a pipette, and the solution was stirred for another
30 minutes. The orange two-phase reaction mixture was then poured into 150 ml of
cold water, and filtered with suction. The precipitated 5-bromovanillin was
washed on the filter with 10 ml HOAc, 100 ml H2O and finally 50 ml of ice-cold
methanol. The precipitate was then sucked as dry as possible and air dried to
give 7.3g (63% of theory) of pale yellow crystals. The methanol wash was diluted
with two volumes of water, and cooled in the freezer to give an additional crop
of orangeish crystals, weighing 0.7g. Total yield 8.0g (70% of theory).
The Cook
Member posted 04-20-99 07:52 PM
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Why don't you just give them the patent number?
PS:They accidentally called it "2,4,5-TriMeOBenzaldehyde" in the title, if you want to look it up...
-cook
Rhodium
Administrator posted 04-21-99 10:17 AM
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Yeah, right! Drone, look in the reference section of my/Osmium's document at
http://rhodium.lycaeum.org/chemistry/mmdamesc.txt (http://rhodium.lycaeum.org/chemistry/mmdamesc.txt)
Overlord
Junior Member posted 04-22-99 09:54 PM
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WOW ! Rev Drone, Rhodium, Osmium and The Cook really know there stuff.
Is there another name for 2,4,5-TriMeOBenzaldehyde
rev drone
Member posted 04-23-99 08:42 AM
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2,4,5-TriMeO benzandelyde is *sometimes* called asaraldehyde, but that's definately not its official name. Not by a longshot. When looking for it, ask for it by the more formal name, 3,4,5-trimethoxybenzaldhyde.
Say, why is it in almost all the refrences we have for making syringaldehyde, people take two steps in converting bromovanillin to syringaldehyde, rathern than do it in one step with sodium methoxide and CuI as a catalyst in DMF? Copper-supported nucleophilic substitution-elimination reactions are a specialty of my research, and if this truly has been overlooked, I'll be happy to supply details. In case I've overlooked it, I appologise in advance.
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-the good reverend drone
rev drone
Member posted 04-23-99 08:47 AM
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Osmium,
I just saw your MMDA contribution's description of exactly what I was dewscribing (almost; I think you method may even be better). Myt mistake. BTW, have you ever looked at the mechanism for that? It involves a Cu(III) intermediate -- wierd.
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-the good reverend drone
Rhodium
Administrator posted 04-23-99 02:06 PM
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Drone, count your substituents one more time.
Overlord: What is used in the making of mescaline is 3,4,5-trimethoxybenzaldehyde,
an this is what can be made from vanillin.
In one patent where this was made, they called it 2,4,5-trimethoxybenzaldehyde (abbreviated 2,4,5-TriMeOBenzaldehyde by the Cook) by mistake. That compound is not what we want to use here.
Rhodium
Administrator posted 04-23-99 02:18 PM
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Drone, btw, are you drunk? Today you seem capable of misspelling your own name if it wasn't in your signature.
*Asarylaldehyde* is the correct inofficial name for 2,4,5-Trimethoxybenzaldehyde.
ChemHack
Member posted 04-23-99 04:58 PM
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3,4,5-trimethoxybenzaldhyde is sold OTC as "Hawian Punch Concentrate."
Ask for it at the supermarket.
heh.
Rhodium
Administrator posted 04-23-99 06:53 PM
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Never buy Aldrich brand Hawaiian Punch. It is very bitter and burns in your throat.
Overlord
Junior Member posted 04-24-99 06:48 PM
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Thanks a million Rhodium ! Found your site on the net and man it's great.
Osmium
Member posted 04-26-99 04:04 AM
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3,4,5-trimethoxybenzaldhyde is sold OTC as "Hawian Punch Concentrate.
This must be a joke, right?
rev drone
Member posted 04-26-99 10:26 AM
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Yeesh! Egads, you're right Rhodium. Sorry about the misspellings. Must be the fumes getting to me.
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-the good reverend drone
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