Sodium Hydroxide → 4-Tetrahydrofuran-3-ylsulfonylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To methyl 4-tetrahydrofuran-3-ylsulfonylbenzoate (1.07 g, 3.96 mmol) in dioxane (11 mL) was added 1 M sodium hydroxide (10.5 mL, 10.5 mmol) and the reaction was heated at 80° C. for 10 minutes. The solvent was evaporated under reduced pressure. The residue was dissolved in water (30 mL) and washed with ethyl acetate (3×25 mL). The aqueous layer was acidified with hydrochloric acid. The aqueous layer was extracted with ethyl acetate (2×30 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield 4-tetrahydrofuran-3-ylsulfonylbenzoic acid (0.86 g, 85%) as a white solid. ESI-MS m/z calc. 256.0. Found 257.3 (M+1)+; Retention time: 0.69 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.59 (s, 1H), 8.19 (d, J=8.3 Hz, 2H), 8.05 (d, J=8.3 Hz, 2H), 4.38-4.15 (m, 1H), 4.06-3.97 (m, 1H), 3.87-3.71 (m, 2H), 3.72-3.54 (m, 1H), 2.20-2.06 (m, 2H).

Provenance & Evidence