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

HRID 1881676Notes

Reaction equation

HRID 1881676 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]>>[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

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 701263,5-Dimethylanisole

Product 1

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

Procedure

A solution of 3,5-dimethylanisole (102.5 g, 753 mmol) in MC (1,000 ml) was cooled to 0° C. A solution of chlorosulfonic acid (251 ml, 3.763 mmol) in MC (250 ml) was added dropwise to this solution. After a reaction time of 10 min, the reaction solution was introduced into an ice bath (1,000 ml), the phases were separated and extraction was carried out once more with MC (250 ml). The combined organic phases were washed with water (1,000 ml) and saturated sodium chloride solution (1,000 ml), dried over Na2SO4 and concentrated. The product was purified by column chromatography over silica gel (heptane/MC 5:1). Yield: 63.5 g, 36%

Workup

  1. additionAfter a reaction time of 10 min, the reaction solution was introduced into an ice bath (1,000 ml)
  2. customthe phases were separated
  3. extractionextraction
  4. washThe combined organic phases were washed with water (1,000 ml) and saturated sodium chloride solution (1,000 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography over silica gel (heptane/MC 5:1)

Sources & evidence

ORD record
ord-85a17bc20b7044db87bde34161ceec4a
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

Loading…