Chlorosulfonic acid → Methyl [4-(chlorosulfonyl)-3,5-dimethylphenoxy]acetate

HRID 1593225Notes

Reaction equation

HRID 1593225 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([CH3:14])[CH:13]=1)[O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[Cl:15][S:16](O)(=[O:18])=[O:17]>>[Cl:15][S:16]([C:13]1[C:12]([CH3:14])=[CH:11][C:4]([O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[CH:3][C:2]=1[CH3:1])(=[O:18])=[O:17]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 13381510Methyl (3,5-dimethylphenoxy)acetate

Product 1

HCID 20786562Methyl [4-(chlorosulfonyl)-3,5-dimethylphenoxy]acetateYield 27%

Conditions

Temperature
-20 °C

Procedure

Methyl (3,5-dimethylphenoxy)acetate (19.4 g, 0.10 mol) was added dropwise over ca. 30 min to rapidly stirred chlorosulfonic acid (58 g, 0.50 mol)that was cooled in a −20° C. bath. After an additional 20 min, the mixture was allowed to slowly warm to room temperature. After 2 hr, the mixture was poured slowly into 400 mL of ice/water. This suspension was extracted with 400 mL of dichloromethane, and the organic layer was washed with water and concentrated. The residue was purified by flash silica gel chromatography (hexanes→dichloromethane) to yield 7.6 g (27%) of the title compound.

Workup

  1. temperatureto slowly warm to room temperature
  2. waitAfter 2 hr
  3. extractionThis suspension was extracted with 400 mL of dichloromethane
  4. washthe organic layer was washed with water
  5. concentrationconcentrated
  6. customThe residue was purified by flash silica gel chromatography (hexanes→dichloromethane)

Sources & evidence

ORD record
ord-a12cad2ed7ac4a9692265d29bea3f9f0
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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