Phenol → 3-[(4-Phenoxyphenyl)sulfonyl]propan-1-ol

HRID 849547Notes

Reaction equation

HRID 849547 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][OH:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:21]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][OH:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 193668741-Propanol, 3-[(4-fluorophenyl)sulfonyl]-

Product 1

HCID 193668023-[(4-Phenoxyphenyl)sulfonyl]propan-1-olYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part C: A solution of 13 g (58 mmol) of 3-[(4-fluorophenyl)sulfonyl]propan-1-ol from part B and 16 g (175 mM) of phenol in 100 mL of anhydrous DMF was purged with nitrogen for one-half hour then treated with 24 g (175 mM) of potassium carbonate. The reaction mixture was then placed in a 100° C. oil bath. After 24 hours, the reaction mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with 1N HCl solution, saturated sodium bicarbonate solution and brine, dried (MgSO4), and concentrated to afford 29 g of crude product. This was chromatographed on silica gel using 30-45% ethyl acetate/hexane to yield 12 g of pure 3-[(4-phenoxyphenyl)sulfonyl]propan-1-ol, m/z=299 (M+Li).

Workup

  1. customwas then placed in a 100° C.
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. washthe organic layer was washed with 1N HCl solution, saturated sodium bicarbonate solution and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto afford 29 g of crude product
  9. customThis was chromatographed on silica gel using 30-45% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e2102c1366d145789d3b196b2bd9fc02
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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