Water → 2'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A 5N aqueous solution of NaOH (10.2 mL, 51.0 mmol) was added into a solution of methyl 2′-methyl-2-(trifluoromethyl)biphenyl-4-carboxylate (5.00 g, 17.0 mmol) in EtOH (150 mL). The resulting mixture was stirred at 60° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure to give a brown solid. The residue was taken up with water (300 mL) and washed twice with EtOAc. The aqueous layer was acidified with a concentrated aqueous solution of HCl until pH=2, and then concentrated until precipitation (half of the volume). The precipitate was filtered off affording the title compound as a beige solid (3.33 g, 70%). 1H NMR (DMSO-d6, 300 MHz) δ 13.55 (br s, 1H), 8.31 (s, 1H), 8.25 (d, J=7.9 Hz, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.37-7.12 (m, 4H), 1.99 (s, 3H). HPLC (Method A), Rt 4.6 min (Purity: 98.7%). UPLC/MS, M−(ESI): 279.2.

Provenance & Evidence