Sodium Hydroxide → 3-Methyl-4-(methylsulfonyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 3-methyl-4-methylsulfonyl-benzoate (5.8 g, 25.4 mmol) in dioxane (25 mL) was added NaOH (20 g, 125.0 mmol) (aq. 25%) and the reaction mixture was heated at 75° C. for 1 hour. The reaction mixture was cooled and was concentrated in vacuo to half the volume and adjusted to pH 2 with 6N HCl solution. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organics were washed with brine solution (50 mL), dried over MgSO4 and concentrated in vacuo to give 3-methyl-4-methylsulfonyl-benzoic acid (5.3 g, 97%) as a white solid. ESI-MS m/z calc. 214.5. found 215.5 (M+1)+; Retention time: 0.67 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.48 (s, 1H), 8.13-7.81 (m, 3H), 3.33 (s, 3H), 2.70 (s, 3H).

Provenance & Evidence