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All 3 posts Subject: OTC! P2P from cinnamaldehyde Please login to post Down

Tengo
(Newbee)
01-12-04 05:17
No 481933
      OTC! P2P from cinnamaldehyde

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.

/T

Rhodium
(Chief Bee)
01-12-04 07:20
No 481949
User Picture       Aldehydes undergo Bayer-Villiger oxidation,...

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...

^{The Hive - Clandestine Chemists Without Borders}

Tengo
(Newbee)
01-12-04 15:31
No 482021
      I understand. Thanks for the input though...

I understand. Thanks for the input though...

/T

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	All 3 posts		Subject: OTC! P2P from cinnamaldehyde		Please login to post		Down


		Tengo (Newbee) 01-12-04 05:17 No 481933				OTC! P2P from cinnamaldehyde
						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. /T



		Rhodium (Chief Bee) 01-12-04 07:20 No 481949				Aldehydes undergo Bayer-Villiger oxidation,...
						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... ^{The Hive - Clandestine Chemists Without Borders}



		Tengo (Newbee) 01-12-04 15:31 No 482021				I understand. Thanks for the input though...
						I understand. Thanks for the input though... /T

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