HCID 66739997, compound → 2-(4-Fluoro-3-methoxyphenyl)-2-methylpropanoic acid

Participants

Reaction Steps

A solution of methyl 2-(4-fluoro-3-methoxyphenyl)-2-methylpropanoate (146 g) in MeOH (2 L) and 25% NaOH in H2O (590 mL) was heated at reflux for 5 h. The reaction mixture was then allowed to cool to room temperature and concentrated at reduced pressure. The residue was dissolved in H2O (2 L) and washed with ether (500 mL). The aqueous layer was acidified cautiously with conc HCl to pH 2. The resulting mixture was extracted with DCM (3 L), and combined extracts were dried over MgSO4, and concentrated at reduced pressure to give 2-(4-fluoro-3-methoxyphenyl)-2-methylpropanoic acid (95 g, 84% over 2 steps). 1H NMR (400 MHz, CDCl3): δ 7.06-7.00 (m, 2H), 6.93 (m, 1H), 3.90 (s, 3H), 3.86 (s, 2H), 1.60 (s, 6H).

Provenance & Evidence