Sodium Hydroxide → 2'-Methyl-2-(methylsulfonyl)biphenyl-4-carboxylic acid
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][C:9]=1[S:18]([CH3:21])(=[O:20])=[O:19].[OH-].[Na+]>C1COCC1.CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=1[S:18]([CH3:21])(=[O:20])=[O:19]Participants
Procedure
Methyl 2′-methyl-2-(methylsulfonyl)biphenyl-4-carboxylate (270 mg; 0.89 mmol; 1 eq.) was dissolved in THF (5 mL) and MeOH (5 mL). sodium hydroxide (0.89 mL; 5 M; 4.44 mmol; 5 eq.) was added and the mixture was stirred at RT overnight. Solvents were evaporated and the crude mixture was partitioned between EtOAc and water. Aqueous phase was acidified with HCl 5N solution. The two phases were separated and the organic phase was washed with brine and dried over MgSO4. After filtration and evaporation of the solvents, the title compound was isolated as a beige solid (215 mg, 83%). 1H NMR (DMSO-d6, 300 MHz) δ 13.53 (br s, 1H), 8.64 (d, J=1.8 Hz, 1H), 8.28 (dd, J=1.8, 8.0 Hz, 1H), 7.49 (d, J=7.91 Hz, 1H), 7.42-7.23 (m, 4H), 2.90 (s, 3H), 2.02 (s, 3H). LC/MS (Method B): 289.2 (M−H)−. HPLC (max plot) 97.9%; Rt 3.83 min.
Workup
- customSolvents were evaporated
- customthe crude mixture was partitioned between EtOAc and water
- customThe two phases were separated
- washthe organic phase was washed with brine
- dry with materialdried over MgSO4
- filtrationAfter filtration and evaporation of the solvents
Sources & evidence
- ORD record
- ord-d6615450d3364a54bddc975ac297daeb
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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