Resveritrol



This is a Heck reaction based on a reaction by Dr Heck and Carl Zeigler:

Reference: Ziegler, Carl B. Jr and Richard F. Heck. Palladium-Catalyzed Vinylic Substitution with Highly Activated Aryl Halides. //The Journal of Organic Chemistry//. July 21, 1978. Volume 43, No. 15. pp 2941-2946.

Meaghan Bartlett

Wow! That was easy! I think the Heck reaction is something that we should cover more in class. It is used quite frequently in synthesis, and it seems to be a versitile way to form a carbon carbon bond. Can you make the 4-hydroxy styrene from a readily available compound with 6 or fewer carbons? Bruce Bondurant



I was working on the synthesis of the 4-hydroxy styrene while you were posting so you overrode my post! This is what I got from the same article I used above. The Heck reaction does seem to be an easy way to form a C-C bond. The common factor between all the Heck reactions seems to be a palladium catalyst.

This is the full synthesis i found, Amber Rosa

Here is an additional synthesis referenced in : A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids. By Guy Solladie,a,* Yacine Pasturel-Jacopea and Jean Maignanb

This is great! The reaction sequence, logic, and description are exactly what I am looking for. Thank you for posting it. Bruce Bondurant