Sodium Hydroxide → 2'-Hydroxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2′-hydroxy-2-methylbiphenyl-4-carboxylate (3 g; 12.38 mmol; 1 eq.) in EtOH (90 mL) at RT was treated with sodium hydroxide (7.43 mL; 5 M; 37.15 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated to give a brown solid. It was taken up in water (250 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with HCl cc to pH 2. Then it was concentrated and extracted with EtOAc giving the title compound as an orange oil. It was purified by flash chromatomatography eluting with EtOAc:cHex (1:1) affording the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 12.88 (br s, 1H), 9.49 (s, 1H), 7.81-7.75 (m, 2H), 7.24-7.18 (m, 2H), 7.05-7.02 (m, 1H), 6.94-6.84 (m, 2H), 2.16 (s, 3H). LC/MS (Method B): 227.2 (M−H)−. HPLC (Method A) Rt 3.26 min (Purity: 95.1%).

Provenance & Evidence