Sodium Hydroxide → 1-Methyl 2,6-dichloro-1,4-benzenedicarboxylate

Participants

Reaction Steps

To a solution of dimethyl 2,6-dichloroterephthalate (186 g, 707 mmol) in THF (600 mL) at room temperature was added a solution of sodium hydroxide (29.7 g, 742 mmol) in water (600 mL). The reaction mixture was stirred at room temperature for 48 hours and concentrated under reduce pressure to a volume of 600 mL. The residue was diluted with water (400 mL), cooled to 0° C. and acidified with 1 N HCl (800 mL). The resulting precipitate was collected by filtration and dried in vacuo to give 3,5-dichloro-4-(methoxycarbonyl)benzoic acid (72 g, yield: 41%) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 3.90 (s, 3H), 7.92 (s, 2H). LCMS (ESI) m/z: 249.0 [M+H+].

Provenance & Evidence