Sodium Hydroxide → 3,5-Dichloro-4-isopropoxybenzoic acid

Participants

Reaction Steps

To a solution of 1.88 g (7.15 mmol) of methyl 3,5-dichloro-4-isopropoxybenzoate (from Step A) in 20 mL of methanol was added 4 mL of 5.0 N sodium hydroxide solution. The mixture was stirred at rt overnight and concentrated. The residue was partitioned between EtOAc (30 mL) and 1 N NaOH (30 mL). The aqueous layer was separated, washed with EtOAc (2×30 mL), acidified using 5.0 N HCl until pH=1, and then extracted with EtOAc (3×30 mL). Organic layers were combined, dried over MgSO4, and concentrated to give 1.51 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.43 (d, J=6.2, 6H), 4.79 (m, 1H), 8.07 (s, 2H).

Provenance & Evidence