Author Topic: Making trimethoxybenzaldehyde  (Read 5164 times)

0 Members and 1 Guest are viewing this topic.

Grimble_Gromble

  • Guest
Making trimethoxybenzaldehyde
« on: September 16, 2001, 09:01:00 PM »
Hi,

I need help!

Anyone knows how can I make trimethoxybenzaldehyde from veratraldehyde?

Thanks

Karl

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #1 on: September 16, 2001, 09:04:00 PM »
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

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #2 on: September 16, 2001, 09:28:00 PM »
See

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html

, and adapt the discourse to veratraldehyde.

You can also see

Post 214077 (missing)

(foxy2: "Re: MANY More compounds to come!", Chemistry Discourse)

Antoncho

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #3 on: September 17, 2001, 09:35:00 AM »
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

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #4 on: September 17, 2001, 02:58:00 PM »
NaI3??? KI3??? It's fanta-chemistry!

hypo

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #5 on: September 17, 2001, 03:03:00 PM »
hm? afaik I3- exists.

PEYOTE

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #6 on: September 17, 2001, 03:16:00 PM »
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

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #7 on: September 17, 2001, 03:21:00 PM »
now come on... that's a little nitpicking, isnt it  :)  i've found chemists do often write down things that only exist in theory.

PEYOTE

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #8 on: September 17, 2001, 03:25:00 PM »
But ONLY in theory...  it's a poetry license

;)

Antoncho

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #9 on: September 17, 2001, 04:32:00 PM »
hey, all i meant was a good query for a search

Rhodium

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #10 on: September 18, 2001, 03:38:00 AM »
According to

Post 214369 (missing)

(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

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #11 on: September 18, 2001, 07:52:00 AM »

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

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #12 on: September 18, 2001, 01:41:00 PM »
p-methoxybenzaldehyde is also a valid starting material, dibromate it and then use 'the usual' procedure (that one from vaniline)

Post 199571 (missing)

(hest: "Re: 3,4,5 Trimethoxybenzaldehyde Synth", Chemistry Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html


https://www.thevespiary.org/rhodium/Rhodium/chemistry/345-tmb.html



PEYOTE

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #13 on: September 18, 2001, 04:26:00 PM »
But if there is someone that don't know that???

Simplicity is the best way to reach maximum yields

Rhodium

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #14 on: September 18, 2001, 05:38:00 PM »
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

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #15 on: September 18, 2001, 05:42:00 PM »
Na+ I3-

eh eh  ;)

Rhodium

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #16 on: September 18, 2001, 05:44:00 PM »
Te-hee. Forgot to change that sign, as there are no button for superscript minus sign in the message composing button collection  :-[

foxy2

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #17 on: September 18, 2001, 10:14:00 PM »
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

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #18 on: September 19, 2001, 04:28:00 PM »
ups, just checked my notes, yor'e right foxy2. Its 4-hydroxy-bensaldehyde. With the methoxy you have to brominate in boiling chlorobenzene :-)

obituary

  • Guest
Re: Making trimethoxybenzaldehyde
« Reply #19 on: September 19, 2001, 11:46:00 PM »
Rhodium, you can use the superscript button and the (-) short dash on the upper part of the keyboard (right of the numbers)   SO4-2