Selective esterification of the polyphenol resveratrol at the 4′-position

Selective esterification of the polyphenol resveratrol was performed under thermodynamic conditions using NaH and acid anhydrides to directly access 4′-esters. Standard conditions with acetyl chloride and pyridine showed poor selectivity, favoring esterification at the 3-position. The extended 4′-phenolate anion is generated in preference to the 3-phenolate under the new anhydride-sodium hydride-DMSO conditions. Acylation occurs to access the 4′-ester products with modest selectivity and yield with minimal formation of the 3-monoester, 3,5-diester, and triester products.