Octylbenzene → Benzenesulfonyl chloride, 4-octyl-

HRID 1966910Notes

Reaction equation

HRID 1966910 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:15][S:16](O)(=[O:18])=[O:17]>C(Cl)(Cl)Cl>[CH2:7]([C:1]1[CH:6]=[CH:5][C:4]([S:16]([Cl:15])(=[O:18])=[O:17])=[CH:3][CH:2]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 16607OctylbenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 11098208Benzenesulfonyl chloride, 4-octyl-Yield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-phenyloctane (5.86 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 80% yield) was used without further purification in the next reaction; 1H NMR (300 MHz, CDCl3) δ 0.87 (t, 3H, J=7 Hz), 1.27-1.32 (m, 10H), 1.64-1.66 (m, 2H), 2.72 (t, 2H, J=8 Hz), 7.42 (d, 2H, J=8 Hz), 7.93 (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-5e06c03218454f0cb22142071f7befb2
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

Loading…