Acetic Acid → 1-[4-(3,3,5,5-Tetramethylcyclohexyl)phenyl]ethanone

HRID 1071917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071917
Cl[Si](C)(C)C.O[C:7]1([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]([CH3:16])([CH3:15])[CH2:8]1.[I-].[Na+].C(O)(=O)C>C(#N)C.[Zn]>[CH3:13][C:11]1([CH3:14])[CH2:10][C:9]([CH3:15])([CH3:16])[CH2:8][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)[CH2:12]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 223904201-[4-(Hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

Produkt 1

HCID 223904281-[4-(3,3,5,5-Tetramethylcyclohexyl)phenyl]ethanoneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

38.1 ml of chlorotrimethylsilane are added over 45 minutes to a solution of 40.45 g of 1-[4-(hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone (compound V′.1) and 56.21 g of sodium iodide in 230 ml of anhydrous acetonitrile. During the addition, the temperature is maintained between 35° C. and 40° C. After stirring for 2 hours, 40 ml of acetonitrile and 39.4 ml of acetic acid are added. Next, 29.4 g of finely powdered zinc are added portionwise with stirring and at room temperature. The reaction mixture is refluxed with vigorous stirring for 4 hours. After cooling to room temperature, the reaction medium is filtered through Celite and then washed with saturated aqueous sodium bicarbonate solution. The organic phase is concentrated under reduced pressure and the oil obtained is purified by chromatography on a column of silica gel, eluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture; yield=68% ; m.p.=54° C. The following compounds are obtained in the same way:

Aufarbeitung

  1. additionDuring the addition
  2. temperaturethe temperature is maintained between 35° C. and 40° C
  3. stirringwith stirring and at room temperature
  4. temperatureThe reaction mixture is refluxed
  5. stirringwith vigorous stirring for 4 hours
  6. filtrationthe reaction medium is filtered through Celite
  7. washwashed with saturated aqueous sodium bicarbonate solution
  8. concentrationThe organic phase is concentrated under reduced pressure
  9. customthe oil obtained
  10. customis purified by chromatography on a column of silica gel
  11. washeluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture
  12. customThe following compounds are obtained in the same way

Quellen und Nachweise

ORD-Eintrag
ord-bcc95865f78244be8ee353f2f4406c36
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908914B1

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