Question Oxidation of alpha Methyl Cinnamaldehyde using H2O2 to P2P ???

skanderbeg

Buying through escrow
New seller
Language
🇬🇧
Joined
Oct 14, 2022
Messages
90
Reaction score
42
Points
18
Hello I have read somewhere probably in the Hive probably 10 years ago or more that there is a way to oxidize alpha methyl cinnamaldehyde using H2O2 ??? Probably a Bayer Villiger reaction not sure. Asking this because I can buy this reagent ( CAS: 101-39-3 ) for 40$ kg as much as I want safely and as far as I remember it was 90% yield reaction or more. Please somebody answer!
 

Osmosis Vanderwaal

Moderator in US section
Resident
Joined
Jan 15, 2023
Messages
1,945
Solutions
4
Reaction score
1,457
Points
113
Deals
1
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!
1DhBUkXZGK

Now look at this picture
Asg9XYqVzD

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!!!!!
 
Top