Water → 4-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

HRID 2059902Notes

Reaction equation

HRID 2059902 reaction equation
[S:1]([Cl:5])(=O)(=[O:3])[OH:2].[CH3:6][C:7]1[CH:8]=[C:9]([O:14][CH3:15])[CH:10]=[C:11]([CH3:13])[CH:12]=1.O>ClCCl>[CH3:15][O:14][C:9]1[CH:10]=[C:11]([CH3:13])[C:12]([S:1]([Cl:5])(=[O:3])=[O:2])=[C:7]([CH3:6])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 701263,5-Dimethylanisole

Product 1

HCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Chlorosulfuric acid (2.3 eq) in dichloromethane (0.5 ml/mmol) was slowly added dropwise over 10 min to a solution of 3,5-dimethylanisol (1 eq) in dichloromethane (1 ml/mmol) cooled to 0° C. The reaction mixture was stirred for a further 10 min and then slowly dropped into iced water (5 eq relative to chlorosulfuric acid). The phases were separated and the aqueous phase extracted with dichloromethane (repeatedly, UV analysis). The combined organic phases were dried (Na2SO4) and concentrated to small volume under vacuum. Yield: 82%

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted with dichloromethane (repeatedly, UV analysis)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-7a33a6c390484ca89e7972b5e0097de7
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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