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

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2′-methyl-2-(trifluoromethyl)biphenyl-4-carboxylate (5.0 g, 17.0 mmol) in EtOH (150 mL) at RT was treated with a 5N aqueous solution of sodium hydroxide (10.2 mL, 51 mmol). The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated to give a brown solid which was taken up in water (300 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with a concentrated aqueous solution of HCl (pH-2), then it was concentrated until precipitation (half of the volume). The suspension was filtered affording the title compound as a beige solid. 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). LC/MS (Method A): 278.9 (M−H)−. HPLC (Method A) Rt 4.57 min (Purity: 98.7%).

Provenance & Evidence