Hydrochloric Acid → 1-Methoxy-4-(phenylsulfonyl)benzene

HRID 1463275Notes

Reaction equation

HRID 1463275 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([S:11](Cl)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[C:16]1([O:22][CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:5]1([S:11]([C:19]2[CH:20]=[CH:21][C:16]([O:22][CH3:23])=[CH:17][CH:18]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 7519AnisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 43517701-Methoxy-4-(phenylsulfonyl)benzeneYield 101%

Procedure

To a solution of 16 g of AlCl3 dissolved in 21.6 g of anisol was added dropwise 17.6 g of benzenesulfonyl chloride. The reaction mixture was heated to reflux for 8 hours and poured into 1N HCl solution containing ice. The resultant solution was extracted with ethyl acetate (100 ml×3), washed with 100 ml of saturated NaHCO3 aqueous solution, dried over Na2SO4 and concentrated to obtain residue, which was recrystallized from hexane-ethyl acetate to obtain 25 g of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 hours
  3. additioncontaining ice
  4. extractionThe resultant solution was extracted with ethyl acetate (100 ml×3)
  5. washwashed with 100 ml of saturated NaHCO3 aqueous solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto obtain residue, which
  9. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-013762765cf44166b51e6f1302e28bdc
Source dataset
uspto-grants-1994_04
Patent number
US05300511

Reaction notes

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