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All 6 posts Subject: Styrene Derivatives by Aromatic Chloroalkylation Please login to post Down

Rhodium
(Chief Bee)
10-31-03 20:07
No 468021
User Picture       Styrene Derivatives by Aromatic Chloroalkylation
(Rated as: excellent)

Chloroalkylation of Phenol Ethers & Synthesis of Methoxystyrenes (Part 1)
Raymond Quelet
Bull. Soc. Chim. France 196-205 (1940) (https://www.rhodium.ws/pdf/chloroalkylation1.pdf)

Chloroalkylation of Phenol Ethers & Synthesis of Methoxystyrenes (Part 2)
Raymond Quelet
Bull. Soc. Chim. France 205-215 (1940) (https://www.rhodium.ws/pdf/chloroalkylation2.pdf)

imp
(Newbee)
10-31-03 20:15
No 468023
      Thanks so much

Thank you Rhodium.

So, what do you think about 1,2-methylenedioxybenzene to isosafrole?? SWIM is curious to hear your opinion.

Maybe that Friedel-Crafts reagent is going to cause some cleavage. Also, the yield would be quite low unless we can make some 'improvisations' to the reaction.

Rhodium
(Chief Bee)
10-31-03 20:26
No 468026
User Picture       Well worth a try!

It's possible... If the MD ring cleavage would be too great, then one could just switch to a milder Lewis Acid like TiCl₄ and try again.

ning
(Hive Bee)
11-03-03 21:18
No 468542
      if its easy to de-hydrochlorinate that sucker...

Then the supported-ZnCl2 direct allylation method just got even easier, by removing the need for the supported Na2CO3! Grrrrreat!

imp
(Newbee)
11-03-03 23:04
No 468565
      Well...

SWIM sees a couple of obstacles...

1. The paper by Quelet says that dehydrochlorination is done using pyridine. If we had pyridine in the first place, then eugenol --> safrole would be a much better idea.

2. We need to buy/make 1-propanal.

Once SWIM saw the dreaded 'p' word (pyridine) in the article, her/his heart just dropped frown . Is there any other way to dehydrohalogenate that chloropropyl group?

Rhodium
(Chief Bee)
11-03-03 23:09
No 468568
User Picture       Dehydrohalogenation with KOtBu

This works, but will instead yield propenylbenzene: https://www.rhodium.ws/chemistry/allylbenzene.html

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	All 6 posts		Subject: Styrene Derivatives by Aromatic Chloroalkylation		Please login to post		Down


		Rhodium (Chief Bee) 10-31-03 20:07 No 468021				Styrene Derivatives by Aromatic Chloroalkylation (Rated as: excellent)
						Chloroalkylation of Phenol Ethers & Synthesis of Methoxystyrenes (Part 1) Raymond Quelet Bull. Soc. Chim. France 196-205 (1940) (https://www.rhodium.ws/pdf/chloroalkylation1.pdf) Chloroalkylation of Phenol Ethers & Synthesis of Methoxystyrenes (Part 2) Raymond Quelet Bull. Soc. Chim. France 205-215 (1940) (https://www.rhodium.ws/pdf/chloroalkylation2.pdf)



		imp (Newbee) 10-31-03 20:15 No 468023				Thanks so much
						Thank you Rhodium. So, what do you think about 1,2-methylenedioxybenzene to isosafrole?? SWIM is curious to hear your opinion. Maybe that Friedel-Crafts reagent is going to cause some cleavage. Also, the yield would be quite low unless we can make some 'improvisations' to the reaction.



		Rhodium (Chief Bee) 10-31-03 20:26 No 468026				Well worth a try!
						It's possible... If the MD ring cleavage would be too great, then one could just switch to a milder Lewis Acid like TiCl₄ and try again.



		ning (Hive Bee) 11-03-03 21:18 No 468542				if its easy to de-hydrochlorinate that sucker...
						Then the supported-ZnCl2 direct allylation method just got even easier, by removing the need for the supported Na2CO3! Grrrrreat!



		imp (Newbee) 11-03-03 23:04 No 468565				Well...
						SWIM sees a couple of obstacles... 1. The paper by Quelet says that dehydrochlorination is done using pyridine. If we had pyridine in the first place, then eugenol --> safrole would be a much better idea. 2. We need to buy/make 1-propanal. Once SWIM saw the dreaded 'p' word (pyridine) in the article, her/his heart just dropped . Is there any other way to dehydrohalogenate that chloropropyl group?



		Rhodium (Chief Bee) 11-03-03 23:09 No 468568				Dehydrohalogenation with KOtBu
						This works, but will instead yield propenylbenzene: https://www.rhodium.ws/chemistry/allylbenzene.html

All 6 posts	End of thread	Top