Chlorosulfonic acid → 2-Ethoxy-5-methylbenzene-1-sulfonyl chloride

HRID 1738759Notes

Reaction equation

HRID 1738759 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)[CH3:2].[Cl:11][S:12](O)(=[O:14])=[O:13]>ClCCl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[S:12]([Cl:11])(=[O:14])=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 73955Benzene, 1-ethoxy-4-methyl-

Product 1

HCID 183661972-Ethoxy-5-methylbenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6.8 g (50 mmol) of 4-ethoxytoluene in 20 mL of dichloromethane was added to a solution of 10 mL (150 mmol) of chlorosulfonic acid in 10 mL of dichloromethane at 0° C. with cooling and stirring. The mixture was stirred 1 hour at 0° C. and was then warmed to ambient temperature and stirred another hour. The resulting tan solution was poured into 200 mL of ice water and the mixture was extracted with dichloromethane. The extract was dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The residual 7.9 g (68 percent of theory) of light tan solid melting at 59-61° C. was the title compound.

Workup

  1. temperaturewith cooling
  2. stirringThe mixture was stirred 1 hour at 0° C.
  3. stirringstirred another hour
  4. extractionthe mixture was extracted with dichloromethane
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-be22829148114abcbdb955a86fd0709d
Source dataset
uspto-grants-1999_10
Patent number
US05965490

Reaction notes

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