Chlorosulfonic acid → 5-tert-Butyl-2-methoxybenzene-1-sulfonyl chloride

HRID 543383Notes

Reaction equation

HRID 543383 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Cl:13][S:14](O)(=[O:16])=[O:15]>C(Cl)Cl>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([S:14]([Cl:13])(=[O:16])=[O:15])[C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 94750p-tert-Butylanisole

Product 1

HCID 132102315-tert-Butyl-2-methoxybenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

12.3 g (0.075 mol) of 4-(1,1-dimethylethyl)anisole, dissolved in 30 ml of methylene chloride, are added dropwise, while cooling in ice, to 16.5 ml of chlorosulfonic acid dissolved in 20 ml of methylene chloride. The mixture is stirred for 40 minutes and then poured onto ice-water. The organic phase is separated off, washed with water, dried with MgSO4 and evaporated. Recrystallization from toluene/petroleum ether provides crystals of melting point: 75°-77° C.

Workup

  1. additionare added dropwise
  2. additionpoured onto ice-water
  3. customThe organic phase is separated off
  4. washwashed with water
  5. dry with materialdried with MgSO4
  6. customevaporated
  7. customRecrystallization from toluene/petroleum ether
  8. customprovides crystals of melting point: 75°-77° C.

Sources & evidence

ORD record
ord-f9f199b4c65f4ba5ba2aa44d9e2f1c25
Source dataset
uspto-grants-1987_04
Patent number
US04661636

Reaction notes

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