Sulfuric Acid → 4-(3-Fluorophenyl)butanoic acid

Participants

Reaction Steps

Hydrogenate a mixture of 4-(3-fluoro-phenyl)-but-3-enoic acid (22 g, 122 mmol), concentrated sulfuric acid (24 ml), and 5% palladium on carbon (3.58 g) in tetrahydrofuran (470 ml) at 60 psi at room temperature overnight. After filtration of the catalyst, remove most of the tetrahydrofuran by rotary evaporation, dilute the residue with ether, wash with water (2×), dry over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (22.50 g, 100%). NMR (400 MHz, CDCl3): δ 1.98 (m, 2H), 2.38 (t, 2H), 2.65 (t, 2H), 6.88 (m, 2H), 6.96 (d, 1H), 7.23 (m, 1H).

Provenance & Evidence