Lithium Hydroxide → 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 a mixture of THF (40 mL)/water (20 mL)/MeOH (20 mL) and 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 concentrated in vacuo. The residue was dissolved in water and cooled to 0° C. and treated with 1 M HCl solution (to pH 3). The resulting precipitate was filtered, 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); 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