The Journal of Organic Chemistry

Acetoacetylation with 2, 2, 6-trimethyl-4H-1, 3-dioxin-4-one: a convenient alternative to diketene

RJ Clemens, JA Hyatt

Index: Clemens, Robert J.; Hyatt, John A. Journal of Organic Chemistry, 1985 , vol. 50, # 14 p. 2431 - 2435

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Citation Number: 186

Abstract

In 1952, Carroll and Bader reported that diketene and acetone react to afford a 1: l adduct, 2, 2, 6-trimethyl-4H-1, 3-dioxin-Cone (l), and that this latter compound would acetoacetylate alcohols in the presence of p-toluenesulfonic acid. 3 Carroll found dioxinone 1 to be slightly more reactive than acetoace@ te esters but much less reactive than diketene. It did not appear that acetoacetylation with dioxinone 1 offered any advantages over ...