Chlorosulfonic acid → 4-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

HRID 1645236Notes

Reaction equation

HRID 1645236 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Cl:11][S:12](O)(=[O:14])=[O:13]>C(Cl)Cl>[CH3:10][O:9][C:4]1[CH:5]=[C:6]([CH3:8])[C:7]([S:12]([Cl:11])(=[O:14])=[O:13])=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 701263,5-Dimethylanisole

Product 1

HCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3,5-dimethylanisole (102.5 g, 753 mmol) in DCM (1000 ml) was cooled to 0° C. A solution of chlorosulfonic acid (251 ml, 3763 mmol) in DCM (250 ml) was added dropwise to this solution. After a reaction time of 10 min, the reaction solution was added to an ice bath (1000 ml), and the phases were separated and extracted again with DCM (250 ml). The combined organic phases were washed with water (1000 ml) and saturated sodium chloride solution (1000 ml), dried over Na2SO4 and concentrated. The product was purified by column chromatography on silica gel (heptane/DCM 5:1). Yield: 63.5 g, 36%

Workup

  1. additionAfter a reaction time of 10 min, the reaction solution was added to an ice bath (1000 ml)
  2. customthe phases were separated
  3. extractionextracted again with DCM (250 ml)
  4. washThe combined organic phases were washed with water (1000 ml) and saturated sodium chloride solution (1000 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography on silica gel (heptane/DCM 5:1)

Sources & evidence

ORD record
ord-827102c1240146cdacdd8e34ce0fe4f7
Source dataset
uspto-grants-2012_02
Patent number
US08124624B2

Reaction notes

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