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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)

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.

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.

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

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?

This works, but will instead yield propenylbenzene:

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