Adamantane → Adamantane-1-sulfinyl Chloride

HRID 36486

Reaction equation

HRID 36486 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-132d52926e864bb082d78664c42f3ae1
Source dataset
uspto-grants-1995_05
Patent number
US05414132

Linked notes

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