It was reported that Dakin-West reaction of glycine forms acetamidoacetone (Hepworth, J.D. Org. Syn. 1965, 45, 1-3). However, in reinvestigation of the reaction we have found that refluxing of glycine with acetic anhydride in pyridine results in diacetamidoacetone, not acetamidoacetone. A suspension of glycine (25 g, 0.33 mmol) in pyridine (162 mL) and acetic anhydride (366 mL) was heated under reflux for 6 h and then concentrated under reduced pressure. The residue was distilled at high vacuum to give diacetamidoacetone (29 g, 56% yield). This work clarifies the inconsistence in previous literature reports and gives correct structure assignment as well as possible reaction mechanistic explanation.

Reinvestigation of Dakin-West reaction of glycine

242nd National Meeting (2011)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.