Butylbenzene → 4-Butylbenzene-1-sulfonyl chloride

HRID 631071

Reaktionsgleichung

Reaktionsgleichung von HRID 631071
[CH2:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[Cl:11][S:12](O)(=[O:14])=[O:13]>C(Cl)(Cl)Cl>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 7705ButylbenzeneHCID 24638Chlorosulfonic acid

Produkt 1

HCID 27373524-Butylbenzene-1-sulfonyl chlorideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of butylbenzene (4.13 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 88% yield) was used without further purification in the next reaction; 1H NMR (300 MHz, CDCl3) δ 0.94 (t, 3H, J=7 Hz), 1.34-1.41 (m, 2H), 1.62-1.67 (m, 2H), 2.73 (t, 2H, J=8 Hz), 7.41 (d, 2H, J=8 Hz), 7.94 (d, 2H, J=8 Hz).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-694c6c993aaa4ade9931da77cc8664f0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320734B2

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