Author Topic: Styrene Derivatives by Aromatic Chloroalkylation  (Read 816 times)

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Rhodium

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Styrene Derivatives by Aromatic Chloroalkylation
« on: October 31, 2003, 09:07:00 PM »


Chloroalkylation of Phenol Ethers & Synthesis of Methoxystyrenes (Part 1)
Raymond Quelet

Bull. Soc. Chim. France 196-205 (1940)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/chloroalkylation1.pdf)

Chloroalkylation of Phenol Ethers & Synthesis of Methoxystyrenes (Part 2)
Raymond Quelet

Bull. Soc. Chim. France 205-215 (1940)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/chloroalkylation2.pdf)

imp

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Thanks so much
« Reply #1 on: October 31, 2003, 09:15:00 PM »
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

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Well worth a try!
« Reply #2 on: October 31, 2003, 09:26:00 PM »
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

  • Guest
if its easy to de-hydrochlorinate that sucker...
« Reply #3 on: November 03, 2003, 10:18:00 PM »
Then the supported-ZnCl2 direct allylation method just got even easier, by removing the need for the supported Na2CO3! Grrrrreat!

imp

  • Guest
Well...
« Reply #4 on: November 04, 2003, 12:04:00 AM »
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

  • Guest
Dehydrohalogenation with KOtBu
« Reply #5 on: November 04, 2003, 12:09:00 AM »
This works, but will instead yield propenylbenzene:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/allylbenzene.html