Sodium Hydroxide → 4-Tetrahydrofuran-3-ylsulfonylbenzoic acid
Reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([S:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:2]1.[OH-].[Na+]>O1CCOCC1>[O:1]1[CH2:5][CH2:4][CH:3]([S:6]([C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)(=[O:8])=[O:7])[CH2:2]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
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).
Workup
- customThe solvent was evaporated under reduced pressure
- dissolutionThe residue was dissolved in water (30 mL)
- washwashed with ethyl acetate (3×25 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (2×30 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c3b734789fb943c3a646522da92219ed
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181273B2
Reaction notes
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