Water → 2-Benzylcyclohexan-1-one

HRID 1279899

Reaktionsgleichung

Reaktionsgleichung von HRID 1279899
[NH2-].[Na+].[C:3]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(OCC)C>[CH2:10]([CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:3]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 7967CyclohexanoneHCID 24533Sodium amide

Produkt 1

HCID 989452-Benzylcyclohexan-1-oneAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Sodium amide (15.6 g, 0.4 mol) was added portionwise to a solution of cyclohexanone (39.26 g, 1.46 mL, 0.4 mol) in 350 mL of anhydrous diethyl ether. The resulting suspension was heated under reflux for 3 h after which time benzyl chloride (46.8 g, 42.6 mL, 0.37 mol) was rapidly added. The mixture was heated under reflux for a further 5 h, then cooled and poured into cold water. The organics were washed once with a dilute HCI solution, a dilute sodium bicarbonate solution and finally with water. The organic layer was dried, filtered and the ether was removed to give 2-benzylcyclohexanone as an oil (28 g, 40%).

Aufarbeitung

  1. temperatureThe resulting suspension was heated
  2. additionwas rapidly added
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for a further 5 h
  5. temperaturecooled
  6. washThe organics were washed once with a dilute HCI solution
  7. customThe organic layer was dried
  8. filtrationfiltered
  9. customthe ether was removed

Quellen und Nachweise

ORD-Eintrag
ord-eeb688a28d2846bbbbb20b9b5da9bc8e
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448424B1

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