Transformation of Aryl Acyloin O‐Alkyl and O‐Phenyl Derivatives to Ketones

Abstract

The treatment of aryl acyloin (α‐hydroxyketone) O‐alkyl and O‐phenyl derivatives with 2–3 equiv of Zn and 1–2 equiv of NH₄Cl in ethanol, refluxing for 20–120 min, gave the corresponding ketones with excellent yields. Further, α,β‐epoxy ketones can be efficiently transformed to β‐hydroxy ketones, and 2,2‐dialkoxy‐1‐phenyl ketone also can be dealkoxylated to 1‐phenyl ketone.

Keywords:

• aryl acyloin O‐derivatives
• deoxygenation
• 2,2‐dialkoxy‐1‐phenyl ethanone
• α,β‐epoxy ketones

Acknowledgments

We gratefully acknowledge financial support from the State Key Program of Basic Research of China (Grant 2002CB512802), the National Natural Science Foundation of China (Grants 20372069, 29725203, and 20472094), the Basic Research Project for Talent Research Group from the Shanghai Science and Technology Commission, the Key Project from the Shanghai Science and Technology Commission (Grant 02DJ14006), the Key Project for New Drug Research from Chinese Academy of Sciences (CAS), and the 863 Hi‐Tech Program (Grants 2002AA233061, 2002AA104270, 2002AA233011, and 2003AA235030).