The Vespiary
The Hive => Novel Discourse => Topic started by: Tengo on January 11, 2004, 09:17:00 PM
-
The idea is to epoxidize cinnamaldehyde with percarbonate, followed by a reduction of the aldehyde group clemmensen-style... Under such harsh conditions the ring will open, producing a diol... Now this can be dehydrated, forming P2P.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000481933-file_r4ga.gif)
/T
-
First step: Not only can the cinnamaldehyde be oxidized by that reagent to cinnamic acid, but the formed epoxyaldehyde can also be oxidized, giving epoxy-cinnamic acid. I believe your proposed reaction is capable of producing a really big mess.
Second step: There is no literature precedence of any (substituted or not) epoxycinnamaldehyde being reduced to anything with a methyl group on the end, neither with the epoxide intact nor with it opened to the glycol.
As I have told other newbees a thousand times over - do not post a lot of "theoretically possible" routes to interesting chemicals without backing it up with literature references where others have performed a very similar procedure to prove the reaction to be practically feasible. Anyone with a little chemistry knowledge can draw up hundreds of diagrams like the one you just made, some of which may work and some of which fail - they are however useless to anyone unless the general concept is proven in practice.
Thus, please do not post anything like the above, unless you for example have a reference where someone successfully has reduced an epoxy-aldehyde to the corresponding propanediol in good yield, as a proof of concept...
-
I understand. Thanks for the input though...
/T