Dichloromethane → 5-tert-Butyl-2-methylbenzene-1-sulfonyl chloride

HRID 543371Notes

Reaction equation

HRID 543371 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Cl:12][S:13]([OH:16])(=O)=[O:14].[CH2:17](Cl)Cl>>[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([S:13]([Cl:12])(=[O:16])=[O:14])[C:8]([CH3:17])=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 73934-tert-ButylphenolHCID 24638Chlorosulfonic acid

Product 1

HCID 51688795-tert-Butyl-2-methylbenzene-1-sulfonyl chloride

Procedure

12.3 g (0.075 mol) of 4-(1,1-dimethylethyl)phenol in 30 ml of methylene chloride are added dropwise, 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. The product is recrystallized from toluene petroleum ether.

Workup

  1. additionpoured onto ice-water
  2. customThe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried with MgSO4
  5. customevaporated
  6. customThe product is recrystallized from toluene petroleum ether

Sources & evidence

ORD record
ord-c4399c49ebf2467a9128d8151eef1df5
Source dataset
uspto-grants-1987_04
Patent number
US04661636

Reaction notes

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