Sodium Hydroxide → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate (40.0 g, 148 mmol) in EtOH (1.2 L) at RT was treated with a 5N aqueous solution of NaOH (90 mL, 450 mmol). The reaction mixture was stirred at 60° C. for 1 hour, and then concentrated under reduced pressure. The yellow solid was taken up with water (800 mL) and washed twice with EtOAc. The aqueous layer was acidified with a concentrated aqueous solution of HCl until pH=2 and was extracted with EtOAc (2×400 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated affording the title compound as a yellow solid (35.1 g, 92%). HPLC (Method A), Rt 4.5 min (Purity: 96.4%). UPLC/MS, M−(ESI): 255.2. 1H NMR (DMSO-d6, 300 MHz) δ 12.99 (br s, 1H), 8.09 (s, 1H), 7.91 (m, 1H), 7.33-7.22 (m, 4H), 7.09 (m, 1H), 4.11 (m, 2H), 3.18 (s, 3H), 1.99 (s, 3H).

Provenance & Evidence