tetraiodide
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Synthsys of 2-hydroxy-4,5-dimethoxy benzaldehyde
I'm working on creating 2-hydroxy-4,5-dimethoxy benzaldehyde from 3,4-dimethoxyphenol. (created by methylation then oxidation of vanillin) what in
trying to predict is if I'm using a reimer-timann or duff formylation, which side of the hydroxyl it will most likely attack, if there's a way to
increase the yeld of the 2-hydroxy-4,5-dimethoxy product over the 2,3-methoxy-6-hydroxy byproduct. Does anyone know how to predict that? I'm also open
to suggestions for other formylation reactions if anyone knows of more selective or higher yealding options.
Also, FIRST POST WOO!
[Edited on 9-6-2018 by tetraiodide]
[Edited on 9-6-2018 by tetraiodide]
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CuReUS
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Both should give you what you want.If you want ease of synthesis,do RT.For higher yield,go for duff.
another method using DMF - https://pubs.acs.org/doi/10.1021/ja9050444
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tetraiodide
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That's an idea, although I started to look at other synthsyses of coumarin and realised it would be a lot easier to synth 6-bromo veratraldehyde from
vanillin and then do the copper catalyzed conversion to the phenol instead, it may be better yealding as well.
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CuReUS
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Quote: Originally posted by tetraiodide  | | I started to look at other synthsyses of coumarin and realised it would be a lot easier to synth 6-bromo veratraldehyde from vanillin and then do the
copper catalyzed conversion to the phenol instead |
you can make coumarin from vanillin in 3 steps-
1.methylate the OH -
https://www.sciencedirect.com/science/article/pii/S004040201...
2.Convert the CHO to OH -https://www.sciencedirect.com/science/article/pii/S004040200...
3.https://en.wikipedia.org/wiki/Pechmann_condensation
alternatively,you can make it in one step from esculetin-https://onlinelibrary.wiley.com/doi/abs/10.1002/cmdc.2010002...
esculetin -https://en.wikipedia.org/wiki/Aesculetin
extraction-https://www.cabdirect.org/cabdirect/abstract/20133050853
[Edited on 10-6-2018 by CuReUS]
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tetraiodide
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I actully wasn't planing on synthesizing coumarin, it's just that your post
made me realise that my target was a potential intermediate in it's synthesis so I just started looking there. Although I just may give it a try,
highly florescent compounds have always fascinated me.
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CuReUS
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| Quote: Originally posted by tetraiodide | | it's just that your post made me realise that my target was a potential intermediate in it's synthesis so I just started looking there.
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I don't understand.What's you target compound ?
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Waffles SS
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All possible way for synthesis 2-hydroxy-4,5-dimethoxy benzaldehyde By reaxys
[Edited on 16-6-2018 by Waffles SS]
Attachment: 2-hydroxy-4,5-dimethoxy benzaldehyde.pdf (125kB)
This file has been downloaded 916 times
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