Sec-Butylbenzene → 4-(Butan-2-yl)benzene-1-sulfonyl chloride

HRID 1925701Notes

Reaction equation

HRID 1925701 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:17][S:18](O)(=[O:20])=[O:19]>ClCCCl>[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([S:18]([Cl:17])(=[O:20])=[O:19])=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8680Sec-ButylbenzeneHCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 37760484-(Butan-2-yl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of commercially available sec-butylbenzene (1.34 g; 10 mmol) in 1,2-dichloroethane (50 mL) was added phosphorus pentachloride (2.5 g; 12 mmol) followed by chlorosulfonic acid (1.3 mL; 20 mmol) slowly. The mixture was heated at 80° C. overnight, then cooled to room temperature and mixed with ice water (150 mL). The organic phase was separated, and the aqueous phase was extracted with dichloromethane (2×10 mL). The organic phases were combined and dried over magnesium sulfate and concentrated under reduced pressure to give an orange oil which was used without further purification (2.3 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with dichloromethane (2×10 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an orange oil which
  7. customwas used without further purification (2.3 g)

Sources & evidence

ORD record
ord-b8e394d90157493fba6a2bb1d270ca01
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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