Pyridine → Phenyl vinyl sulfone

HRID 1075497

Reaktionsgleichung

Reaktionsgleichung von HRID 1075497
[C:1]1([S:7]([CH2:10][CH2:11]O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]1([S:7]([CH:10]=[CH2:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 302022-(Phenylsulfonyl)ethanolHCID 516892Sodium Bicarbonate

Produkt 1

HCID 79664Phenyl vinyl sulfoneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-(phenylsulfonyl)ethanol (143.8 g, purity 96.2%, 743 mmol) was added to 71.9 g of toluene, and 30.0 g (38 mmol) of pyridine was added to the mixture. The resulting solution was heated to 60° C., then 110.5 g (929 mmol) of thionyl chloride added over 5 hours at 60 to 70° C., and the mixture was stirred for 2 hours at 70° C. Then, the mixture was diluted with 143.9 g of toluene and cooled to 45° C. Then 303.2 g of 7% sodium bicarbonate solution and 193.4 g of toluene were added, washed separated. Obtained organic layer was mixed with 303.2 g of 7% sodium bicarbonate solution and stirred and separated. 5 g of the organic layer was sampled and subjected to HPLC analysis, which revealed that (β-chloroethylsulfonyl)benzene was obtained in a yield of 98% and phenylvinylsulfone in a yield of 0.7%. (Internal Standard: methyl benzoate).

Aufarbeitung

  1. additionwas added to the mixture
  2. temperaturecooled to 45° C
  3. washwashed
  4. customseparated
  5. additionObtained organic layer was mixed with 303.2 g of 7% sodium bicarbonate solution
  6. stirringstirred
  7. customseparated
  8. aliquot5 g of the organic layer was sampled

Quellen und Nachweise

ORD-Eintrag
ord-9456b4a8742c442b87542d0c5aa9de23
Quelldatensatz
uspto-grants-1999_05
Patentnummer
US05902905

Verknüpfte Notizen

Wird geladen…