Hi,

I need help!

Anyone knows how can I make trimethoxybenzaldehyde from veratraldehyde?

Thanks

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

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)

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

NaI3??? KI3??? It's fanta-chemistry!

hm? afaik I₃^- exists.

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.

now come on... that's a little nitpicking, isnt it    i've found chemists do often write down things that only exist in theory.

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

hey, all i meant was a good query for a search

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.

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

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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.

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

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

Simplicity is the best way to reach maximum yields

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⁺

Na⁺ I₃^-

eh eh  

Te-hee. Forgot to change that sign, as there are no button for superscript minus sign in the message composing button collection  

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

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Do Your Part To Win The War

ups, just checked my notes, yor'e right foxy2. Its 4-hydroxy-bensaldehyde. With the methoxy you have to brominate in boiling chlorobenzene :-)

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