Sciencemadness Discussion Board

Phenol to salicaldahyde how?

HankTheHam - 13-7-2023 at 06:32

I’m trying to convert aspirin to benzaldehyde and I have it all figured out except for the conversion of phenol to salicaldehyde then salicaldehyde to benzaldehyde I know about the Reimer–Tiemann reaction and that’s the route I’m wanting to take so if anyone here has any experience with this help with the set up and measurements of chemicals would be appreciated

Edit:Never mind I found a paper on this that explains everything in good detail from what I have heard this reaction is a horrible way to prepare salicaldehyde so I’m going to do it just for the challenge
[Edited on 13-7-2023 by HankTheHam]

[Edited on 13-7-2023 by HankTheHam]

arkoma - 13-7-2023 at 08:43

From here https://www.sciencemadness.org/madscifaq.html#2.1_Board_topi...
Quote:
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RustyShackleford - 13-7-2023 at 10:40

Dont do reimer tiemann, it blows. i posted about my experience here: http://www.sciencemadness.org/talk/viewthread.php?tid=61964&...
i recommend doing the Mg mediated formylation instead.

HankTheHam - 13-7-2023 at 14:55

Alright upon further analysis my post sounds really sketchy I’m not a meth head looking for a quick high or someone looking to make money I’m just a really Amateur chemist who had an idea for a project I didn’t think about it too hard I was smelling some almond extract and liked the smell knowing it was benzaldehyde producing the smell I put together the outline to a synthesis of benzaldehyde from aspirin I’m pretty amateur so I don’t have a big chemist vocabulary so I came here asking for some help on a step I was stuck on sorry about my demeanor

clearly_not_atara - 14-7-2023 at 05:31

The ortho-formylation of interest in drug synthesis is just one of five or six steps, depending on the precursors, and it's one of the easier ones. Furthermore, you don't start with plain phenol.

So I don't think that this particular reaction should be so scrutinized, particularly since the OP didn't even mention the compound which is actually a precursor.

Salicylaldehyde to benzaldehyde is likely to be very hard, though. Consider a different target.