Reaktion #64764

Reaktionsgleichung

Aluminum trichloride

thionyl chloride

Adamantane

→

1-Adamantane sulfinyl chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was cooled to -20°
2. 2
   SonstigeAfter the thionyl chloride was removed under vacuum
3. 3
   workup.ADDITIONthe residue was diluted with CCl4
4. 4
   SonstigeThe layers were separated
5. 5
   Waschenand the organic layer was washed (brine)
6. 6
   Trocknendried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under vacuum
9. 9
   workup.DISTILLATIONThe residue was distilled under vacuum (1 torr, 133.3 Pascals) with a vigreaux column
10. 10
    Sonstigeto give the product (28.8 g; bp 118°-128°) as a waxy solid

Vorschrift

Aluminum trichloride (40 g, 3 mol) was added slowly to thionyl chloride (200 ml, 2.7 mol), and the mixture was cooled to -20°. Adamantane was added in portions over 21/2 hrs, and the resulting mixture was stirred 1 hr and allowed to warm to room temperature. After the thionyl chloride was removed under vacuum, the residue was diluted with CCl4 ; and the aluminum trichloride was decomposed with ice and water. The layers were separated; and the organic layer was washed (brine), dried (Na2SO4), filtered, and concentrated under vacuum. The residue was distilled under vacuum (1 torr, 133.3 Pascals) with a vigreaux column to give the product (28.8 g; bp 118°-128°) as a waxy solid; TLC, Rf =0.6-0.4, EtOAc:hexanes (15:85).

Quelle