Adamantane → Adamantane-1-sulfinyl Chloride

HRID 1165523

Reaction equation

HRID 1165523 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[S:5]([Cl:8])(Cl)=[O:6].[CH:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2>>[C:9]12([S:5]([Cl:8])=[O:6])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2

Participants

4

Reactant 3

HCID 9238AdamantaneHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 4737333Adamantane-1-sulfinyl Chloride

Procedure

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).

Workup

  1. temperaturethe mixture was cooled to -20°
  2. customAfter the thionyl chloride was removed under vacuum
  3. additionthe residue was diluted with CCl4
  4. customThe layers were separated
  5. washand the organic layer was washed (brine)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. distillationThe residue was distilled under vacuum (1 torr, 133.3 Pascals) with a vigreaux column
  10. customto give the product (28.8 g; bp 118°-128°) as a waxy solid

Sources & evidence

ORD record
ord-3f3168bfe7564e60ac8f03a55eb46228
Source dataset
uspto-grants-1990_03
Patent number
US04910190

Linked notes

Loading…