Grimble_Gromble (Stranger)
09-16-01 21:01
No 214061
      Making trimethoxybenzaldehyde  Bookmark   

Hi,

I need help!

Anyone knows how can I make trimethoxybenzaldehyde from veratraldehyde?

Thanks
 
 
 
 
    Karl
(Newbee)
09-16-01 21:04
No 214062
      Re: Making trimethoxybenzaldehyde  Bookmark   

I think you can brominate and treat in the same way as vanillin to prepare the 345TMBz as described on Rhodium's site...if thats what you want to know
 
 
 
 
    PEYOTE
(Hive Bee)
09-16-01 21:28
No 214073
      Re: Making trimethoxybenzaldehyde  Bookmark   

See ../rhodium/chemistry /mmda.mescaline.html , and adapt the discourse to veratraldehyde.

You can also see Post 214077 (foxy2: "Re: MANY More compounds to come!", Chemistry Discourse)
 
 
 
 
    Antoncho
(Official Hive Translator)
09-17-01 09:35
No 214267
      Re: Making trimethoxybenzaldehyde  Bookmark   

There's a much better way recently discussed here, using NaI and I2 in water. It is one-stage and higher-yielding than the above proc's - UTSE.

A good query would bee "NaI3 or KI3"

Antoncho
 
 
 
 
    PEYOTE
(Hive Bee)
09-17-01 14:58
No 214333
      Re: Making trimethoxybenzaldehyde  Bookmark   

NaI3??? KI3??? It's fanta-chemistry!
 
 
 
 
    hypo
(Hive Bee)
09-17-01 15:03
No 214336
      Re: Making trimethoxybenzaldehyde  Bookmark   

hm? afaik I3- exists.
 
 
 
 
    PEYOTE
(Hive Bee)
09-17-01 15:16
No 214340
      Re: Making trimethoxybenzaldehyde  Bookmark   

yes, but if u write NaI3 it seems that AT THE SOLID STATE may exist this salt, and it is wrong (ar, I've never heard that NaI3 exist like a solid salt). In soln may exist Na+ and I3- (well [I3]-), but not NaI3... it's dissociated. Like with K.

 
 
 
 
    hypo
(Hive Bee)
09-17-01 15:21
No 214342
      Re: Making trimethoxybenzaldehyde  Bookmark   

now come on... that's a little nitpicking, isnt it smile i've found chemists do often write down things that only exist in theory.
 
 
 
 
    PEYOTE
(Hive Bee)
09-17-01 15:25
No 214344
      Re: Making trimethoxybenzaldehyde  Bookmark   

But ONLY in theory...  it's a poetry license

wink
 
 
 
 
    Antoncho
(Official Hive Translator)
09-17-01 16:32
No 214357
      Re: Making trimethoxybenzaldehyde  Bookmark   

hey, all i meant was a good query for a search
 
 
 
 
    Rhodium
(Chief Bee)
09-18-01 03:38
No 214547
      Re: Making trimethoxybenzaldehyde  Bookmark   

According to Post 214369 (foxy2: "2 Bromination of 3,4-dimethoxybenzaldehyde", Chemistry Discourse), bromination of veratraldehyde (3,4-dimethoxybenzaldehyde) produces 2-bromo-4,5-dimethoxybenzaldehyde instead. It seems vanillin is the correct starting material fror 3,4,5-trimethoxybenzaldehyde.
 
 
 
 
    terbium
(Old P2P Cook)
09-18-01 07:52
No 214619
      Re: Making trimethoxybenzaldehyde  Bookmark   


yes, but if u write NaI3 it seems that AT THE SOLID STATE may exist this salt, and it is wrong



It is not "wrong". It is a short-hand convention used by people who know enough not to need trivial details restated at every opportunity.

 
 
 
 
    hest
(Hive Bee)
09-18-01 13:41
No 214726
      Re: Making trimethoxybenzaldehyde  Bookmark   

p-methoxybenzaldehyde is also a valid starting material, dibromate it and then use 'the usual' procedure (that one from vaniline)
Post 199571 (hest: "Re: 3,4,5 Trimethoxybenzaldehyde Synth", Chemistry Discourse)
../rhodium/chemistry /mmda.mescaline.html
../rhodium/chemistry /345-tmb.html
 
 
 
 
    PEYOTE
(Hive Bee)
09-18-01 16:26
No 214778
      Re: Making trimethoxybenzaldehyde  Bookmark   

But if there is someone that don't know that???

Simplicity is the best way to reach maximum yields
 
 
 
 
    Rhodium
(Chief Bee)
09-18-01 17:38
No 214805
      Re: Making trimethoxybenzaldehyde  Bookmark   

Then they should consult the suggested links or look in the literature before stating incorrect things. If you had performed the suggested search for NaI3, you would have found credible papers on the use of the substance. Any inorganic chem book would tell you that in solution, NaI and I2 combines to form Na+ I3+
 
 
 
 
    PEYOTE
(Hive Bee)
09-18-01 17:42
No 214809
      Re: Making trimethoxybenzaldehyde  Bookmark   

Na+ I3-

eh eh wink
 
 
 
 
    Rhodium
(Chief Bee)
09-18-01 17:44
No 214811
      Re: Making trimethoxybenzaldehyde  Bookmark   

Te-hee. Forgot to change that sign, as there are no button for superscript minus sign in the message composing button collection blush
 
 
 
 
    foxy2
(Distinctive Doe)
09-18-01 22:14
No 214867
      Re: Making trimethoxybenzaldehyde  Bookmark   

I think the 4-methoxy is more difficult to brominate than a 4-hydroxy and therefor much harder to dibrominate.  A while back G_Pig told me it was not worth the effort to try to dibrominate 4-methoxyPEA (gosh i think it was that).  He said the yeild sucked.

Some of the literature I have looked at seems to indicate this as well



Do Your Part To Win The War
 
 
 
 
    hest
(Hive Bee)
09-19-01 16:28
No 215135
      Re: Making trimethoxybenzaldehyde  Bookmark   

ups, just checked my notes, yor'e right foxy2. Its 4-hydroxy-bensaldehyde. With the methoxy you have to brominate in boiling chlorobenzene :-)
 
 
 
 
    obituary
(Hive Addict)
09-19-01 23:46
No 215270
      Re: Making trimethoxybenzaldehyde  Bookmark   

Rhodium, you can use the superscript button and the (-) short dash on the upper part of the keyboard (right of the numbers)   SO4-2