Selective alkylations of certain phenolic and enolic functions with lithium carbonate/alkyl halide

WE Wymann, R Davis, JW Patterson Jr…

Index: Wymann, Walter E.; Davis, Roman; Patterson, John W.; Pfister, Juerg R. Synthetic Communications, 1988 , vol. 18, # 12 p. 1379 - 1384

Full Text: HTML

Citation Number: 47

Abstract

Abstract Phenolic groups with pKa≤ 8 (due to the presence of electron withdrawing groups in the orho-or para-position) can be alkylated selectively with Li2CO3/alkyl halide/DMF; less acidic phenolic groups are unreactive. Even though chelated phenolic/enolic functions have unexpectedly high experimental pKa′ s (∼ 10), they can be alkylated with this reagent combination.