I recently performed the glycidylation of some polyphenols. And I just read a paper (Doi: Article Study of the O-glycidylation of natural phenolic compounds. ...
). I'm really confused about the chemical structure of the side-product with the benzodioxane structure. I've drawn it in the attached file. Could anyone tell me why?
Trieu Phu Hau
Because Base can make a link with proton alpha (proton near epoxy group in the graph). Pyrogalol can become a Carbocation. This carbocation is stable. Next, the 2nd hydroxyl group of pyrogalol can react with this carbocation. That cause the making of a hexagonal ring (in stereochemistry, hexagonal ring is stable). So I think this is the mechanism you need.
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Yunfan Zhang
Trieu Phu Hau Thank you Mr. Trieu. I agree with you. But in the original paper, the aliphatic OH group was close to the C1 but not C2 (I drew the chemical structure of the product in the dotted box). I don't know why.
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