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Natural Science Forum / Chemistry / Organic Synthesis / October 2003Synthesis of Vanillin
Hi, I'm interested in synthesising some vanillin (4-hydroxy-3-methoxybenzaldehyde) from eugenol (1-(4-hydroxy-3-methoxyphenyl)-2-propene, I think) and was wondering what methods are possible to oxidise 1-(4-acetyl-3-methoxyphenyl)-2-propene to acetylvanillin or even isoeugenol directly to vanillin. Can anyone suggest some methods? Thanks Nathan  SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Maybe: 1.first ,protect OH group then KMnO4 oxidize it to R-Ph-COOH,then LiAlH4 to R-Ph-CH2OH,to R-Ph-CHO 2. O3 to R-Ph-CH2-CHO,then react with NH2OH to decrease a carbon.you can find this reaction in your textbook . "Nathan Stanley" <freezedream@hotmail.com> дÈëÏûÏ¢ÐÂÎÅ :bfjto9$8o@panther.Gsu.EDU... > Hi, I'm interested in synthesising some vanillin > (4-hydroxy-3-methoxybenzaldehyde) from eugenol > (1-(4-hydroxy-3-methoxyphenyl)-2-propene, I think) and was wondering what > methods are possible to oxidise 1-(4-acetyl-3-methoxyphenyl)-2-propene to > acetylvanillin or even isoeugenol directly to vanillin. > Can anyone suggest some methods? > Thanks > Nathan "Nathan Stanley" <freezedream@hotmail.com> дÈëÏûÏ¢ÐÂÎÅ :bfjto9$8o@panther.Gsu.EDU... > Hi, I'm interested in synthesising some vanillin > (4-hydroxy-3-methoxybenzaldehyde) from eugenol > (1-(4-hydroxy-3-methoxyphenyl)-2-propene, I think) and was wondering what > methods are possible to oxidise 1-(4-acetyl-3-methoxyphenyl)-2-propene to > acetylvanillin or even isoeugenol directly to vanillin. > Can anyone suggest some methods? > Thanks > Nathan SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Hello Nathan, I know that this isn't much help, but have you looked at purchasing Vanillin? I've been using it as starting material for polyphenols (as have numerous researchers), and it is quite cheap at Aldrich. Best regards, Peter SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Hello Nathan, I know that this isn't much help, but have you looked at purchasing Vanillin? I've been using it as starting material for polyphenols (as have numerous researchers), and it is quite cheap at Aldrich. Best regards, Peter SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA reducers, complexants, antioxydants... john wrote: > just out of interest whats the interest in polyphenols? > > Hello Nathan, > > I know that this isn't much help, but have you looked at purchasing > > Vanillin? I've been using it as starting material for polyphenols (as > > have numerous researchers), and it is quite cheap at Aldrich. > > Best regards, > > Peter SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Some one making mescaline :P > reducers, complexants, antioxydants... > john wrote: > > just out of interest whats the interest in polyphenols? > > > Hello Nathan, > > > I know that this isn't much help, but have you looked at purchasing > > > Vanillin? I've been using it as starting material for polyphenols (as > > > have numerous researchers), and it is quite cheap at Aldrich. > > > Best regards, > > > Peter SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA |
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