Syntheses of Aryl Glyoxylate. I. The Reaction of Alkyl Dichloro(alkoxy)acetates with Aromatics in the Presence of Lewis Acid

Ethyl dichloro(ethoxy)acetate (1) and methyl dichloro(methoxy)acetate (2) were characterized. The reaction of 1 and 2 with aromatics in the presence of AlCl3 gave a considerable yield of aromatic α-keto ester. The aromatics included mono- and polymethylbenzene and anisol. The reaction was studied under various conditions and the results were compared with the acylation by ethoxalyl or methoxalyl chloride. The reaction mechanism was also discussed.