chlorination using bleach? -rev drone , Hive Novel Discourse


		dormouse (Member) 04-23-00 02:43 No 108699				chlorination using bleach? -rev drone	Bookmark
						the Hive BB Novel Discourse chlorination using bleach? profile \| register \| preferences \| faq \| search next newest topic \| next oldest topic Author Topic: chlorination using bleach? rev drone Member posted 04-19-99 05:04 PM -------------------------------------------------------------------------------- Here's the deal. Mescaline analogs like escaline and proscaline are really interesting, and I'd like to see an inexpensive, practical OTC synthetic route. Now, all of these are made from their nitrostyrenes, which are made from their benzaldehydes (4-alkoxy-3,5-dimethoxybenzaldehydes), and all their benzaldehydes are made from syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde), which is made from either 3-bromo- or 3-chloro-4-hydroxy-5-methoxybenzaldehyde with sodium methoxide. The aforementioned halogen-containing compounds are made by either brominating or chlorinating vanillin, and all that is pretty straight forward, ifyou start with bromine or chlorine as your halogen source. Here's was I was thinking as a prctical variation: Can sodium or calcium hypochloride be used as the halogen source? A sort of in situ chlorine generation could be accomplished by adding some acid to a solution of the hypochloride, and that should do it, n'est pas? Has anyone seen examples of this? This has other pracical applications, of course; pretty slick if it works, eh? ------------------ -the good reverend drone Cherrie Baby Member posted 04-20-99 01:08 AM -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- Osmium, The search engine isn't showing anything. Do you know the url of the posted results? What were the conditions? ------------------ -the good reverend drone Rhodium Administrator posted 04-20-99 03:58 PM -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- Yeah, right! Drone, look in the reference section of my/Osmium's document at http://rhodium.lycaeum.org/chemistry/mmdamesc.txt Osmium Member posted 04-21-99 11:23 AM -------------------------------------------------------------------------------- Hey Rhodium, there is another patent which you gave me, it uses only half the stoichometric amount of Br2 and reoxidises the formed Br(-) with bleach, H2O2 or HNO3. This one inspired me to the idea of trying it without Br2, but using KBr and H2O2 instead. This one is essential for this procedure. Rhodium Administrator posted 04-22-99 07:39 AM -------------------------------------------------------------------------------- Isn't that patent in our reference list? Then I don't know which one it is... Osmium Member posted 04-22-99 10:45 AM -------------------------------------------------------------------------------- US 4.551.558 It's not in the ref. section. Overlord Junior Member posted 04-22-99 09:54 PM -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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. ------------------ -the good reverend drone rev drone Member posted 04-23-99 08:47 AM -------------------------------------------------------------------------------- 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. ------------------ -the good reverend drone Rhodium Administrator posted 04-23-99 02:06 PM -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- Thanks a million Rhodium ! Found your site on the net and man it's great. Osmium Member posted 04-26-99 04:04 AM -------------------------------------------------------------------------------- 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 -------------------------------------------------------------------------------- Yeesh! Egads, you're right Rhodium. Sorry about the misspellings. Must be the fumes getting to me. ------------------ -the good reverend drone All times are CT (US) next newest topic \| next oldest topic Administrative Options: Close Topic \| Archive/Move \| Delete Topic Hop to: Select a Forum or ArchiveList of Forums:General DiscussionAcquisition DiscourseChemistry DiscourseMethods DiscourseNovel DiscourseCrystal MethSerious Chemistry ForumThe Hive CouchSerious Tryptamine DiscourseAdmin Chill-out TentList of Archives:Couch ArchivesClassics!Law and OrderThe litter box.misc. PEAs Contact Us \| the Hive Powered by: Ultimate Bulletin Board, Version 5.39a © Infopop Corporation (formerly Madrona Park, Inc.), 1998 - 1999.