Sodium Iodide → 1-(2-Iodoethyl)adamantane

HRID 128196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 128196
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]23[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]4)[CH2:14]2)[CH2:20]3)(=O)=O)=CC=1.[I-:24].[Na+]>CC(=O)CC>[C:13]12([CH2:12][CH2:11][I:24])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 129106472-(1-Adamantyl)ethyl p-toluene-sulfonate

Produkt 1

HCID 221412941-(2-Iodoethyl)adamantaneAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A solution of 2-(1-adamantyl)ethyl p-toluene-sulfonate (4.0 g) and sodium iodide (2.5 g) in 2-butanone (20 ml) is heated for 2 hours under reflux. The cooled solution is filtered and concentrated to a residue which is partitioned between dichloromethane and water. The organic layer is washed with aqueous sodium thiosulfate and water. The dried solution is evaporated to a crystalline mass which is recrystallized from ethanol to give 2-(1-adamantyl)ethyl iodide (2.0 g), m.p. 93°-94°. An analytical sample is obtained by recrystallization from the same solvent, m.p. 97°-98°.

Aufarbeitung

  1. temperatureunder reflux
  2. filtrationThe cooled solution is filtered
  3. concentrationconcentrated to a residue which
  4. customis partitioned between dichloromethane and water
  5. washThe organic layer is washed with aqueous sodium thiosulfate and water
  6. customThe dried solution is evaporated to a crystalline mass which
  7. customis recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9286b9a633f24e9a8878e7a1d0574623
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259324

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