Water → 4-Chloro-2-methylsulphonyl-3-phenoxybenzoic acid

HRID 1491584Notes

Reaction equation

HRID 1491584 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([S:18]([CH3:21])(=[O:20])=[O:19])[C:10]=1F.O.[OH-].[Li+].O>CN(C)C=O>[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([S:18]([CH3:21])(=[O:20])=[O:19])[C:10]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 168937Lithium hydroxide, monohydrateHCID 544424304-Chloro-3-fluoro-2-methylsulphonylbenzoic acid

Product 1

HCID 189533144-Chloro-2-methylsulphonyl-3-phenoxybenzoic acidYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Phenol (2.26 g) was added to a mixture of 4-chloro-3-fluoro-2-methylsulphonylbenzoic acid (4.46 g) and lithium hydroxide monohydrate (1.65 g) in N,N-dimethylformamide and the mixture was stirred and heated at 100° C. overnight. It was cooled, poured into water and acidified to pH 1, extracted with ethyl acetate and the organic phase extracted into aqueous sodium bicarbonate solution. The aqueous layer was acidified to pH 1 and extracted with ethyl acetate, washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 4-chloro-2-methylsulphonyl-3-phenoxybenzoic acid (4.06 g) as an off-white solid m.p. 231°-235° C.

Workup

  1. temperatureIt was cooled
  2. extractionextracted with ethyl acetate
  3. extractionthe organic phase extracted into aqueous sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried (magnesium sulphate)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-3855a15d00f64d918a1e8212fa63bc87
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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