Methanol → HCID 68153645, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-fluoro-4-(2-hydroxy-2-methyl-propyl)benzoate (1.59 g, 7.03 mmol) was dissolved in THF (40 mL), water (200 mL) and MeOH (21 mL) before LiOH (1.01 g, 42.2 mmol) was added. The reaction mixture was heated at 55° C. for 30 minutes. The reaction mixture was cooled to room temperature and the solvents were removed under reduced pressure. The residue was dissolved in water and cooled in an ice water bath and treated with HCl 1M to pH 3. The resulting precipitate was collected by vacuum filtration, washed with water and dried under high vacuum to yield 3-fluoro-4-(2-hydroxy-2-methyl-propyl)benzoic acid (999 mg, 67%) as a white solid. ESI-MS m/z calc. 212.1, found 211.1 (M+1)+; Retention time: 0.98 minutes (3 min run, scanned using negative ionization mode). 1H NMR (400 MHz, CDCl3) δ 7.84 (dd, J=7.9, 1.6 Hz, 1H), 7.77 (dd, J=10.1, 1.6 Hz, 1H), 7.39 (d, J=15.1 Hz, 1H), 2.91 (s, 2H), 1.28 (s, 6H).

Provenance & Evidence