Question Oxidatie van alfa-methylcinnamaldehyde met H2O2 tot P2P ???

skanderbeg

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Hallo, ik heb ergens in de Hive gelezen, waarschijnlijk 10 jaar geleden of meer, dat er een manier is om alfa-methylcinnamaldehyde te oxideren met H2O2? Waarschijnlijk een Bayer Villiger reactie, ik weet het niet zeker. Ik vraag dit omdat ik dit reagens ( CAS: 101-39-3 ) kan kopen voor 40$ kg zoveel als ik veilig wil en voor zover ik me herinner was het 90% opbrengst reactie of meer. Graag iemand antwoord!
 

Osmosis Vanderwaal

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Yes, you can Bayer-Villager A-methylcinnamaldehyde with H2O2, but it won't get you p-2-p it will get you ....depending on the solvent time and temp, a-methyl-cinnamic acid perhaps (the carboxalic acid) or..I don't know, it's like this......P-2-P is commonly msde from cinnamaldehyde via hydrazine in diethyl glycol, which affords propynal benzene, which is oxidized by H2O2 to P-2-P. If you start at a-methylcinnamaldehyde (notidce the difference is the methyl on the alpha carbon) and go straight to peroxidation, you epoxidize it to 2-(phenoxymethyl)oxirane. Now whats interesting to me is that 2-(phenoxymethyl)oxirane is exactly BMK (benzyl-methyl-ketone) without a methyl and a carboxylic acid on the end. Methyl-carboxylic acid is better known as acetic acid. BUT WAIT THERE'S More!
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Now look at this picture
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this is a picture of epoxide ring opening via several routes. Look at the first on. If R was 2-(phenoxymethyl)oxirane (it can be) and you reacted it with an amine , R'-nh2, you might get something interesting. Especially if R' was methyl (makingg R'-NH2 CH3NH2, methlamine) 1 hydroxy-n-methyl-phenylethylamine. What's that mean? IDK I'm out of time to look, kids got to get on the bus!!!!!
 
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