Lithium Hydroxide → 3-Methyl-4-(morpholin-4-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 3-methyl-4-morpholin-4-ylbenzoate obtained in step 1 (4 g, 169.3 mmol) in THF (100 mL) and water (5 mL) was added lithium hydroxide (2 g, 84.6 mol). The resulting mixture was heated at 50° C. for 12 h. Solvents were removed under vacuum and the resulting mass was diluted with water. The aqueous layer was washed with DCM (2×50 mL) and was acidified with conc HCl (pH=4). It was extracted with EtOAc (2×100 mL). The EtOAc layer was washed with brine and dried over sodium sulfate, affording the title compound as a yellow solid (3.6 g, 97%). 1H NMR (DMSO-d6, 400 MHz) δ 12.5 (bs, 1H), 7.72-7.74 (m, 2H), 7.04-7.06 (m, 1H), 3.72-3.75 (m, 4H), 2.88-2.90 (m, 4H), 2.33 (s, 3H). LC/MS (Method A): 222.1 (M+H)+. HPLC (Method B) Rt 1.42 min (Purity: 98.3%).

Provenance & Evidence