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Synthesis of α-Hydroxyacetophenones

Mark McLaughlin*, Kevin M. Belyk, Gang Qian, Robert A. Reamer and Cheng-yi Chen

*Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., Rahway, New Jersey 07065, United States, Email: mark_mclaughlinmerck.com

M. McLaughlin, J. M. Belyk, G. Qian, R. A .Reamer, C.-y. Chen, J. Org. Chem., 2012, 77, 5144-5148.

DOI: 10.1021/jo3005556 (free Supporting Information)


Abstract

In a general method for the preparation of α-hydroxyacetophenones, functionalized arylmagnesium species are transmetalated to the corresponding arylzinc intermediates, which undergo Cu(I)-catalyzed reaction with acetoxyacetyl chloride. Acidic hydrolysis of the acetate group releases the target α-hydroxyacetophenones with minimal production of undesired polymeric side products.

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Key Words

Aryl Ketones, Hydrolysis


ID: J42-Y2012-1820