Eric Bauch - A General Synthesis of 2-Alkoxy-2-phenylpropanoic Acids

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  Publication Details (including relevant citation   information):

  Keith A. Monk, Nathan C. Duncan,   Eric A. Bauch and Charles M. Garner. Tetrahedron.   2008, 64 (37), 8605-8609


       A preparation of a variety of   2-alkoxy-2-phenylpropanoic acids in two steps is described.   Epoxidation of α-methylstyrene with mCPBA  in   methanol or primary alcohol solvents proceeded with an    acid-catalyzed in situ ring opening reaction to give the   corresponding  2-alkoxy-2-phenyl-1-propanols in 28–91%   yield. Lower yields were  realized with secondary (22–58%)   and tertiary (14%) alcohols. These  alcohols were cleanly   oxidized to the corresponding carboxylic acids  using a mild   Heyns' oxidation (O2, Pt/C) in generally good to   excellent yields (25–92%). The derived   (S)-α-methylbenzylamide  diastereomers are nearly   all well separated by capillary GC, and the  use of this   method to determine the enantiomeric purity of    brucine-resolved 2-methoxy-2-phenylpropanoic acid was   demonstrated.

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