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Author: Subject: Ideas needed - Oxiation of acid sensitive asarone to 2,4,5-trimethoxybenzaldehyde
Sandmeyer
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[*] posted on 23-6-2010 at 12:52


Quote: Originally posted by Nicodem  

In short, I think the Bayer-Villiger on veratraldehyde, O-methylation and Vilsmeier-Haack formylation as proposed by Sandmeyer is a more convenient and reliable route.

[Edited on 23/6/2010 by Nicodem]


Nope, sorry, I never proposed Vilsmeier-Haack, since it is not OTC, I proposed OTC methylation, OTC Baeyer-Villager on veratraldehyde and OTC Duff formylation.

[Edited on 23-6-2010 by Sandmeyer]




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Nicodem
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[*] posted on 24-6-2010 at 00:50


Quote: Originally posted by Sandmeyer  
Nope, sorry, I never proposed Vilsmeier-Haack, since it is not OTC, I proposed OTC methylation, OTC Baeyer-Villager on veratraldehyde and OTC Duff formylation.

Pardon. I had the route in mind rather than the specific reactions and methods. The thing is that Vilsmeier-Haack on 1,2,4-trimethoxybenzene is supported by several literature examples, while I was unable to find examples for the modified Duff. It might work with hexamine/AcOH though, but whether someone prefers OTC or OTS ("of the shelf") depends, not only on what is available in the local shops and on lab shelves, but also which method is already verified. Which is not to say that one should always chose the verified method. For example, I prefer to live on the edge and have a stressful life, so I often chose to check new methods. :D
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