Bis(acetoxy)iodobenzene → 4-tert-Butylcyclohexanone

HRID 1926459

Reaktionsgleichung

Reaktionsgleichung von HRID 1926459
[C:1]12C[CH:5]([C:6]1(C)C)[CH2:4][CH:3]([C:10]1([CH:20]3CC4CC(C4(C)C)=C3C)[CH2:15]C3CC(C3(C)C)=[C:11]1C)[C:2]=2C.C(OC1C(OC(=O)C)=C(I)C=CC=1)(=[O:33])C>C(Cl)(Cl)(Cl)Cl>[C:10]([CH:3]1[CH2:4][CH2:5][C:6](=[O:33])[CH2:1][CH2:2]1)([CH3:20])([CH3:15])[CH3:11]

Komponenten

4

Edukt 2

HCID 21865429Bis(acetoxy)iodobenzeneHCID 534720352,6,6-Trimethyl-3,3-bis(2,6,6-trimethyl-3-bicyclo[3.1.1]hept-1-enyl)bicyclo[3.1.1]hept-1-ene

Produkt 1

HCID 73924-tert-Butylcyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

To a 4-t-butylcyclohexane-1,1-dihydroperoxide and terpinene (trapping reagent) in a stirred room temperature solution of carbon tetrachloride was added, over a period of five to ten minutes, a solution of bisacetoxyiodobenzene (BAIB) in carbon tetrachloride. Rapid bubbling commenced upon addition of the BAIB solution and ceased within a few minutes after addition was completed. Stirring was continued for 0.5 h, after which the solution was filtered through a plug of silica, which was washed with CH2Cl2. The residue obtained upon concentration was purified by column chromatography on silica gel to give 4-t-butyl cyclohexanone and the trapping product ascaridole (endoperoxide of terpinene).

Aufarbeitung

  1. customRapid bubbling
  2. additioncommenced upon addition of the BAIB solution
  3. waitceased within a few minutes
  4. additionafter addition
  5. filtrationafter which the solution was filtered through a plug of silica, which
  6. washwas washed with CH2Cl2
  7. customThe residue obtained upon concentration
  8. customwas purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-37ba5328c74f4ce7aa6f8813dc87a875
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08182785B2

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