Dimethyl Sulfoxide → 4-(4-Fluorophenylsulphonyl)phenol

HRID 224477Notes

Reaction equation

HRID 224477 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[K+].CS(C)=[O:22]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:22])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 67842Benzene, 1,1'-sulfonylbis(4-fluoro-

Product 1

HCID 3438024-(4-Fluorophenylsulphonyl)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bis-(4-fluorophenyl) sulphone (100 g; 0.394 mole), potassium hydroxide solution (91.98 g; 0.787 mole KOH) and dimethyl sulphoxide (400 cm3) were stirred together in a stainless steel vessel under nitrogen at 57° C. for 24 hours. Two liquid phases remained throughout the reaction. The reaction mixture was diluted with water and twice extracted with diethyl ether to recover non-phenolic material (9 g). The aqueous phase was then acidified and the phenolic component (86 g; m.p. 150°-154° C.) was extracted with more ether. By subliming this product under a diffusion pump at 180° C., followed by recrystallisation from toluene (400 cm3), 4-(4-fluorophenylsulphonyl)phenol (72.5 g) was obtained, m.p. 158°-159° C. The potassium salt was obtained from this phenol as a very pale yellow solid.

Workup

  1. customTwo liquid phases remained throughout the reaction
  2. extractiontwice extracted with diethyl ether
  3. customto recover non-phenolic material (9 g)
  4. extractionthe phenolic component (86 g; m.p. 150°-154° C.) was extracted with more ether
  5. customat 180° C.
  6. customfollowed by recrystallisation from toluene (400 cm3)

Sources & evidence

ORD record
ord-6f1659897777421c8377ceedab2a16c3
Source dataset
uspto-grants-1980_11
Patent number
US04232142

Reaction notes

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