Hydrochloric Acid → 3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid

HRID 878113Notes

Reaction equation

HRID 878113 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:5]=1.O.O.[OH-].[Li+].Cl>O1CCOCC1.CCOC(C)=O>[CH3:17][S:14]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=1)[C:3]([OH:18])=[O:2])(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 706632513-Methanesulfonyl-5-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-methanesulfonyl-5-trifluoromethyl-benzoic acid methyl ester (1.0 g, 3.54 mmol) in dioxane (15 mL) was added water (15 mL) and lithium hydroxide monohydrate (186 mg, 4.43 mmol). The reaction mixture was stirred at room temperature for 2 hours and then poured on 100 ml 1M aqueous HCl and 100 mL EtOAc. The layers were separated and the aqueous layer was extracted a second time with 100 mL EtOAc. The organic layers were washed with 100 mL brine, dried over MgSO4, filtered and concentrated under vacuum. Colorless solid (930 mg, 98%). MS (ESI): m/z=266.995 [M−H]−.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted a second time with 100 mL EtOAc
  3. washThe organic layers were washed with 100 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a400b10fe5674caeaa29cad54a448b4f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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