Sodium Hydroxide → (S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acid

HRID 1930976Notes

Reaction equation

HRID 1930976 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17].[OH-].[Na+]>C(O)C>[CH3:13][S:10]([C:8]1[CH:7]=[CH:6][C:5]([O:14][C@@H:15]([CH3:20])[C:16]([F:17])([F:18])[F:19])=[C:4]([CH:9]=1)[C:3]([OH:21])=[O:2])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58863349HCID 58863349, compound

Product 1

HCID 58863351(S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 0.604 mmol 5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid methyl ester in 1.97 ml ethanol was added 1.21 mmol 2 N aq NaOH solution and the reaction mixture was stirred at 80° C. for 0.5 hour. After such time the solvent was removed in vacuo, the residue was taken in water and acidified by addition of 2N HCl to yield after filtration the title compound as a white solid (88%). MS (m/e): 311.0 ([M−H]−, 100%)

Workup

  1. customAfter such time the solvent was removed in vacuo
  2. additionacidified by addition of 2N HCl
  3. customto yield
  4. filtrationafter filtration the title compound as a white solid (88%)

Sources & evidence

ORD record
ord-49b2bb59a638427db48e94ee835d29c0
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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