Benzoic acid, 3-(chlorosulfonyl)- → 2-(4-Methylbenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoate

HRID 2182871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2182871
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[C:14]1([CH3:26])[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH2:24]O)(=[O:22])=[O:21])=[CH:16][CH:15]=1>O=S(Cl)Cl>[C:14]1([CH3:26])[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH2:24][O:9][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[CH:6]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-

Produkt 1

HCID 224793682-(4-Methylbenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoateAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A heterogeneous mixture of 3-chlorosulfonyl-benzoic acid (11.0 g, 50.0 mmol) in 18 mL of SOCl2 was refluxed for 3 h. Thereafter the excess of SOCl2 was removed, the residual brown oil was dissolved in 60 mL of CH3CN, and then 2-(p-tolylsulfonyl)ethanol (9.4 g, 47.0 mmol, 0.95 eq.) was added. The mixture was heated to reflux temperature for 20 h. Thereafter the most of CH3CN was removed, the resulting oil was purified by short column chromatography (silica gel, CH2Cl2) to give light brown oil, which was dried further under vacuum to yield 19.1 g (95%) of a light brown solid.

Aufarbeitung

  1. temperaturewas refluxed for 3 h
  2. customThereafter the excess of SOCl2 was removed
  3. dissolutionthe residual brown oil was dissolved in 60 mL of CH3CN
  4. temperatureThe mixture was heated
  5. temperatureto reflux temperature for 20 h
  6. customThereafter the most of CH3CN was removed
  7. customthe resulting oil was purified by short column chromatography (silica gel, CH2Cl2)
  8. customto give light brown oil, which
  9. customwas dried further under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-39dff0b64d8b4529a63d3e18749547e0
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897227B2

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