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Updated: Apr 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Synthesis of 2-Naphthols via a Trifluoroacetic Acid-Mediated Epoxy Alcohol Rearrangement
Jack B Story1, Kalista E Ringler1, Chi L Nguyen1
1Department of Chemistry, Vassar College, 124 Raymond Avenue, Poughkeepsie, New York 15405, United States.
None:
Epoxy alcohols derived from 2-benzylidene-1-indanones undergo rearrangement to 2-naphthols when exposed to trifluoroacetic acid. The reaction sequence tolerates a variety of functional groups from both the parent indanone and the benzaldehyde derivatives. No chromatographic purification is required until the final synthetic step, and the epoxy alcohol syntheses use only water and alcohols as solvents. The synthesis is operationally simple, and the 2-naphthol products can be easily derivatized into pharmaceutically relevant compounds.
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