Water → HCID 54517002, compound

HRID 343026Notes

Reaction equation

HRID 343026 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([S:12][CH3:13])[C:3]=1[CH:14]([F:16])[F:15].[OH-].[Li+].O>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([S:12][CH3:13])[C:3]=1[CH:14]([F:16])[F:15]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 54012959HCID 54012959, compound

Product 1

HCID 54517002HCID 54517002, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-chloro-3-difluoromethyl-2-methylsulphenylbenzoate (9.1 g) and lithium hydroxide (2.2 g) were dissolved in methanol and water and the mixture stirred overnight at room temperature. The mixture was then evaporated and the residue dissolved in water and washed with ethyl acetate. The aqueous layer was acidified to pH 1 with 2M HCl and extracted with ethyl acetate. The organic extract was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness yielding 4-chloro-3-difluoromethyl-2-methylsulphenylbenzoic acid (8.02 g) as a beige solid NMR (CDCl3) 2.5(s,3H), 7.5(d,1H), 7.65(t,1H), 7.8(d,1H).

Workup

  1. customThe mixture was then evaporated
  2. dissolutionthe residue dissolved in water
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried (anhydrous magnesium sulphate)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-478170e0c0734985acba9250ba192b23
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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