Acetic Acid → 6-(4-Aminobenzene-1-sulfonyl)hexan-1-ol

HRID 1461206Notes

Reaction equation

HRID 1461206 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]C(=O)C)=[CH:7][CH:6]=1)(=O)C.C(O)(=[O:24])C.OO.[OH-:28].[Na+]>C(O)C.O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])(=[O:24])=[O:28])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 57299238HCID 57299238, compound

Product 1

HCID 199800346-(4-Aminobenzene-1-sulfonyl)hexan-1-olYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 145 g (0.47 mol) of (4-acetamidophenyl)-(6-acetoxyhexyl)sulfide and 600 mL of glacial acetic acid was heated at reflux with stirring, and 140 g (1.2 mol) of 30% hydrogen peroxide was added in small portions over 3 hours. The reaction mixture was poured on ice, and an oil separated. The mixture was extracted with dichloromethane and the extract was washed with water. The organic layer was dried (MgSO4) and the solvent was removed at reduced pressure to leave a tan oil. The oil was dissolved in a mixture of 100 g of sodium hydroxide, 260 mL of ethanol, and 140 mL of water, and refluxed with stirring for 16 hours. The product was extracted with ethyl ether and the extract was dried (MgSO4) and concentrated. A waxy solid was obtained which was recrystallized from 60% ethanol/40% water at -20° C. to provide 74 g (61%) of a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. additionThe reaction mixture was poured on ice
  4. customan oil separated
  5. extractionThe mixture was extracted with dichloromethane
  6. washthe extract was washed with water
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent was removed at reduced pressure
  9. customto leave a tan oil
  10. temperaturerefluxed
  11. stirringwith stirring for 16 hours
  12. extractionThe product was extracted with ethyl ether
  13. dry with materialthe extract was dried (MgSO4)
  14. concentrationconcentrated
  15. customA waxy solid was obtained which
  16. customwas recrystallized from 60% ethanol/40% water at -20° C.

Sources & evidence

ORD record
ord-a7ef04527b904481a7d8bf92bd805f50
Source dataset
uspto-grants-1991_12
Patent number
US05075043

Reaction notes

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