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All 10 posts Subject: Nitrostyrenes from Cinnamic Acids Please login to post Down

Rhodium
(Chief Bee)
04-10-04 15:20
No 500069
User Picture       Nitrostyrenes from Cinnamic Acids
(Rated as: good read)

A Nitro-Hunsdiecker Reaction: From Unsaturated Carboxylic Acids to Nitrostyrenes and Nitroarenes
Jaya Prakash Das, Pradipta Sinha, and Sujit Roy
Org. Lett. 4, 3055-3058 (2002) (https://www.rhodium.ws/pdf/cinnamicacid2nitrostyrene.pdf)
Supporting Information (http://pubs.acs.org/subscribe/journals/orlef7/suppinfo/4/i18/ol0262901/ol0262901_s1.pdf)
DOI:10.1021/ol0262901

Abstract
The nitrodecarboxylation of aromatic alpha,beta-unsaturated carboxylic acids and ring-activated benzoic acids can be achieved using nitric acid (3 equiv) and catalytic AIBN (2 mol %) in MeCN.

^{The Hive - Clandestine Chemists Without Borders}

GC_MS
(Hive Addict)
04-11-04 14:56
No 500202
User Picture       wow

Very interesting reaction! laugh

For instance: http://fachschaft.cup.uni-muenchen.de/~schleifi/reaktion/reaction/perkin.html

$

Rhodium
(Chief Bee)
04-19-04 20:02
No 501647
      Cinnamic Acids from Malonic acid/Benzaldehyde
(Rated as: good read)

Synthesis of Cinnamic Acid Derivatives Using Ethanol as Solvent or Microwave Assisted Method
Rolando F. Pellón, Taimirys Mamposo, Erick Gonzalez and Osmar Calderon
Synthetic Communications 30(20), 3769-3774 (2000) (https://www.rhodium.ws/pdf/cinnamic.malonic-mw.pdf)

Abstract
A comparison study about some parameters which influence the condensation of veratraldehyde with malonic acid in the presence of piperidine using ethanol as solvent and microwave irradiation was done, the obtainment of several substituted cinnamic acids are reported.

^{The Hive - Clandestine Chemists Without Borders}

ning
(acetaminophanatic)
04-26-04 14:49
No 503130
User Picture       Or

as mentioned in an earlier post, you could condense benzaldehyde with acetonitrile or ethyl acetate and hydrolyze it to the cinnamic acid. Much more OTC.

BTW, Rhodium, what do you think about replacing that AIBN with benzoyl peroxide or H2O2/Fe(II)? That would bee extremely awesome.

http://www.chem.wisc.edu/areas/reich/handouts/NameReagents/namedreag-cont.htm
Has all the named reagents. Very handy smile

I've been chased by both cops and robbers. So what does that make me?

Rhodium
(Chief Bee)
04-26-04 15:44
No 503134
User Picture       radical initiators

replacing that AIBN with benzoyl peroxide or H2O2/Fe(II)?

I wouldn't add H2O2/Fe²⁺ to that solution (water & inorganic salts might be problematic), but benzoyl peroxide sounds OK. If you look at Fig 1, you can also see that the yields are not floored even if no radical initiator is added.

^{The Hive - Clandestine Chemists Without Borders}

Osmium
(Stoni's sexual toy)
04-26-04 15:52
No 503135
User Picture       AIBN and dibenzoylperoxide have different...

AIBN and dibenzoylperoxide have different decomposition constants. You generally cannot simply substitute one radical initiator with another one and expect the same reaction rate.

BUSH/CHENEY 2004! After all, it ain't my country!

Aurelius
(Active Asperger Archivist)
04-26-04 20:58
No 503181
      chem accounts

there is a good article in chemical accounts that covers the kinetics of different radical initiators, but I don't have the ref with me. If somebody actually wants it, I could post it in the next couple of days.

Act quickly or not at all.

Rhodium
(Chief Bee)
04-26-04 21:23
No 503187
User Picture       I'd be interested in that one, so please post...

I'd be interested in that one, so please post it if you find it.

^{The Hive - Clandestine Chemists Without Borders}

ning
(acetaminophanatic)
04-27-04 04:41
No 503259
User Picture       Yes, that would be nice

this is a cool thread!

Osmium, I'm no chemist, but I think any radical initiator worth its salt should make the reaction "fast enough". Otherwise, why would chemists use it for that purpose?

Rhodium, I doubt water's a problem. That paper says they use "21.35 M HNO3", which weighs 1.345 kg/L, placing its concentration between 50 and 60% w/w according to my merck index. (wierd)

I plan to research the use of the Fenton reagent as radical initiator some more. It would certainly bee the most accesible thing the average bee could get, though benzoyl peroxide can be found by those with excessive acne...

You could basically throw in a little bit of iron powder and H2O2. The nitric acid would make the salt for you, and away you go.

Awesome topic. Combined with an OTC method of reducing nitrostyrenes, I think we could have a real winner in the mescaline dept. here.

I've been chased by both cops and robbers. So what does that make me?

Osmium
(Stoni's sexual toy)
04-28-04 11:21
No 503482
User Picture       > Osmium, I'm no chemist, but I think any...

> Osmium, I'm no chemist, but I think any radical initiator worth its salt
> should make the reaction "fast enough".

You thought wrong.

> Otherwise, why would chemists use it for that purpose?

For the same reason that different hydride reducing agents were invented. Selectivity for example, and to have the desired concentration of radicals present in your reaction at different temperatures and in different solvent systems.

BUSH/CHENEY 2004! After all, it ain't my country!
www.american-buddha.com/addict.war.1.htm

	https://the-hive.archive.erowid.org	the-hive@erowid.org



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	All 10 posts		Subject: Nitrostyrenes from Cinnamic Acids		Please login to post		Down


		Rhodium (Chief Bee) 04-10-04 15:20 No 500069				Nitrostyrenes from Cinnamic Acids (Rated as: good read)
						A Nitro-Hunsdiecker Reaction: From Unsaturated Carboxylic Acids to Nitrostyrenes and Nitroarenes Jaya Prakash Das, Pradipta Sinha, and Sujit Roy Org. Lett. 4, 3055-3058 (2002) (https://www.rhodium.ws/pdf/cinnamicacid2nitrostyrene.pdf) Supporting Information (http://pubs.acs.org/subscribe/journals/orlef7/suppinfo/4/i18/ol0262901/ol0262901_s1.pdf) DOI:10.1021/ol0262901 Abstract The nitrodecarboxylation of aromatic alpha,beta-unsaturated carboxylic acids and ring-activated benzoic acids can be achieved using nitric acid (3 equiv) and catalytic AIBN (2 mol %) in MeCN. ^{The Hive - Clandestine Chemists Without Borders}



		GC_MS (Hive Addict) 04-11-04 14:56 No 500202				wow
						Very interesting reaction! For instance: http://fachschaft.cup.uni-muenchen.de/~schleifi/reaktion/reaction/perkin.html $



		Rhodium (Chief Bee) 04-19-04 20:02 No 501647				Cinnamic Acids from Malonic acid/Benzaldehyde (Rated as: good read)
						Synthesis of Cinnamic Acid Derivatives Using Ethanol as Solvent or Microwave Assisted Method Rolando F. Pellón, Taimirys Mamposo, Erick Gonzalez and Osmar Calderon Synthetic Communications 30(20), 3769-3774 (2000) (https://www.rhodium.ws/pdf/cinnamic.malonic-mw.pdf) Abstract A comparison study about some parameters which influence the condensation of veratraldehyde with malonic acid in the presence of piperidine using ethanol as solvent and microwave irradiation was done, the obtainment of several substituted cinnamic acids are reported. ^{The Hive - Clandestine Chemists Without Borders}



		ning (acetaminophanatic) 04-26-04 14:49 No 503130				Or
						as mentioned in an earlier post, you could condense benzaldehyde with acetonitrile or ethyl acetate and hydrolyze it to the cinnamic acid. Much more OTC. BTW, Rhodium, what do you think about replacing that AIBN with benzoyl peroxide or H2O2/Fe(II)? That would bee extremely awesome. http://www.chem.wisc.edu/areas/reich/handouts/NameReagents/namedreag-cont.htm Has all the named reagents. Very handy I've been chased by both cops and robbers. So what does that make me?



		Rhodium (Chief Bee) 04-26-04 15:44 No 503134				radical initiators
						replacing that AIBN with benzoyl peroxide or H2O2/Fe(II)? I wouldn't add H2O2/Fe²⁺ to that solution (water & inorganic salts might be problematic), but benzoyl peroxide sounds OK. If you look at Fig 1, you can also see that the yields are not floored even if no radical initiator is added. ^{The Hive - Clandestine Chemists Without Borders}



		Osmium (Stoni's sexual toy) 04-26-04 15:52 No 503135				AIBN and dibenzoylperoxide have different...
						AIBN and dibenzoylperoxide have different decomposition constants. You generally cannot simply substitute one radical initiator with another one and expect the same reaction rate. BUSH/CHENEY 2004! After all, it ain't my country!



		Aurelius (Active Asperger Archivist) 04-26-04 20:58 No 503181				chem accounts
						there is a good article in chemical accounts that covers the kinetics of different radical initiators, but I don't have the ref with me. If somebody actually wants it, I could post it in the next couple of days. Act quickly or not at all.



		Rhodium (Chief Bee) 04-26-04 21:23 No 503187				I'd be interested in that one, so please post...
						I'd be interested in that one, so please post it if you find it. ^{The Hive - Clandestine Chemists Without Borders}



		ning (acetaminophanatic) 04-27-04 04:41 No 503259				Yes, that would be nice
						this is a cool thread! Osmium, I'm no chemist, but I think any radical initiator worth its salt should make the reaction "fast enough". Otherwise, why would chemists use it for that purpose? Rhodium, I doubt water's a problem. That paper says they use "21.35 M HNO3", which weighs 1.345 kg/L, placing its concentration between 50 and 60% w/w according to my merck index. (wierd) I plan to research the use of the Fenton reagent as radical initiator some more. It would certainly bee the most accesible thing the average bee could get, though benzoyl peroxide can be found by those with excessive acne... You could basically throw in a little bit of iron powder and H2O2. The nitric acid would make the salt for you, and away you go. Awesome topic. Combined with an OTC method of reducing nitrostyrenes, I think we could have a real winner in the mescaline dept. here. I've been chased by both cops and robbers. So what does that make me?



		Osmium (Stoni's sexual toy) 04-28-04 11:21 No 503482				> Osmium, I'm no chemist, but I think any...
						> Osmium, I'm no chemist, but I think any radical initiator worth its salt > should make the reaction "fast enough". You thought wrong. > Otherwise, why would chemists use it for that purpose? For the same reason that different hydride reducing agents were invented. Selectivity for example, and to have the desired concentration of radicals present in your reaction at different temperatures and in different solvent systems. BUSH/CHENEY 2004! After all, it ain't my country! www.american-buddha.com/addict.war.1.htm

All 10 posts	End of thread	Top