103261-03-6

Usage

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 841, 1995 DOI: 10.1016/0040-4039(94)02395-R

Upstream product

• 64-19-7 acetic acid 
• 349537-53-7 1-acetylamino-1-(2'-chlorophenyl)ethene 
• 24654-08-8 3-(2-chlorophenyl)prop-2-ynoic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 133662-20-1 1-(2-chlorophenyl)-2-hydroxyethanone 
• 32345-65-6 (R)-(2-chlorophenyl)-1,2-ethanediol 

Relevant academic research and scientific papers

Conversion of Aldehydes to α-Acetoxymethyl Ketones: One-carbon Homologation with (Benzotriazol-1-yl)phenoxymethane

Reaction of aldehydes with (benzotriazol-1-yl)phenoxymethyl anion afforded the corresponding addition products which, upon treatment with p-toluenesulfonic acid in acetic acid, yielded the corresponding α-acetoxymethylketones.

Decarboxylative Oxyacyloxylation of Propiolic Acids: Construction of Alkynyl-Containing α-Acyloxy Ketones

Novel decarboxylative oxyacyloxylation of propiolic acids has been developed. This reaction provides an efficient access to alkynyl-containing α-acyloxy ketones from readily available starting materials and exhibits significant functional group tolerance. Furthermore, oxyacyloxylation of terminal alkynes and aliphatic propiolic acids was also developed. A possible reaction mechanism is proposed based on mechanistic studies.

PhI(OAc)2-promoted umpolung acetoxylation of enamides for the synthesis of α-acetoxy ketones

Umpolung is a fundamental concept in organic chemistry, which provides an alternative strategy for the synthesis of target compounds which were not easily accessible by conventional methods. Herein, a mild and efficient PhI(OAc)2-promoted umpolung acetoxylation reactions of enamides was developed for the synthesis of α-acetoxy ketones. The reaction tolerates a wide range of functional groups and affords α-acetoxy ketones in good to excellent yields. PhI(OAc)2 serves as a source of acetoxy in the reaction.

Novel and efficient transformation of enamides into α-acyloxy ketones via an acyl intramolecular migration process

Hydrogen peroxide and anhydride mediated transformation of enamides to afford substituted α-acyloxy ketones is described. This transition-metal-free cascade reaction has a broad substrate scope and high efficiency. The acyl intramolecular migration procedure successfully achieved this acyloxylation process under mild conditions and increased the atom efficiency.