Hexylbenzene → 4-Hexylbenzene-1-sulfonyl chloride

HRID 1854294Notes

Reaction equation

HRID 1854294 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl:13][S:14](O)(=[O:16])=[O:15]>C(Cl)(Cl)Cl>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14109HexylbenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 125827864-Hexylbenzene-1-sulfonyl chlorideYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-hexylbenzene (5.00 g, 30.8 mmol) in CHCl3 (50 mL) was added chlorosulfonic acid (17 mL, 29.8 g, 256 mmol) and the mixture was stirred at rt for 20 h. The mixture was poured on ice (200 mL) and extracted with EtOAc (3×100 mL). The combined extracts were washed with water, a solution of NaHCO3, and water, dried (Na2SO4), and concentrated in vacuo. The yellow oily residue (ca 81% yield) was used without further purification in the next reaction; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=7 Hz), 1.30-1.35 (m, 6H), 1.55-1.63 (m, 2H), 2.59 (t, 2H, J=8 Hz), 7.38 (d, 2H, J=8 Hz), 7.89 (d, 2H, J=8 Hz).

Workup

  1. additionThe mixture was poured on ice (200 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined extracts were washed with water
  4. dry with materiala solution of NaHCO3, and water, dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc740ef47be84e909b2040169d75d060
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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