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

HRID 1018800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1018800
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 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.

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 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

Quellen und Nachweise

ORD-Eintrag
ord-8c7d06312a5f4e58894b2201f733aefc
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06482986B1

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