Hydrogen Peroxide → HCID 15260033, Verbindung

HRID 1448015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448015
[CH3:1][C:2]1([CH3:10])[C:8](=[CH2:9])[C:6](=[CH2:7])[CH2:5][CH2:4][CH2:3]1.[BH4-].[Na+].B(F)(F)F.[H-].[OH-:18].[Na+].OO>COCCOCCOC.O>[CH2:7]=[C:6]1[CH2:5][CH2:4][CH2:3][C:2]([CH3:10])([CH3:1])[CH:8]1[CH2:9][OH:18].[OH:18][CH2:7][CH:6]1[CH2:5][CH2:4][CH2:3][C:2]([CH3:10])([CH3:1])[C:8]1=[CH2:9]

Komponenten

10

Edukt 6

HCID 784Hydrogen PeroxideHCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 166653HydrideHCID 4311764Sodium borohydrideHCID 103131641,1-Dimethyl-2,3-dimethylidenecyclohexane

Produkt 2

HCID 111264862,2-Dimethyl-6-methylenecyclohexanemethanolHCID 15260033HCID 15260033, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8150DiglymeLösungsmittel2×

Versuchsvorschrift

Delta-Pyronene (27.2 g.) in 100 ml diglyme was stirred at 25° C. with 2.3 g. NaBH4, and a solution of 10.1 ml BF3 etherate in 16 ml diglyme was added thereto over a period of 30 minutes. After completion of the addition, the reaction mixture was stirred for 1 hour at 25° after which excess hydride was decomposed with 20 ml H2O. Sodium hydroxide (22 ml of 13% solution) then was added followed by the addition of 20 ml of 30% H2O2 over a 20-30 minute period. This mixture was stirred for 1 hour at 25°-30°. Workup of this mixture involved extraction with 150 ml ether and washing with 10% NaCl solution. Solvent removal under reduced pressure provided 30 g of crude product which was fractionated at 10 mm on a Nester-Faust spinning band column to give 6.7 g pure 1-methylene-2-hydroxymethyl-3,3-dimethylcyclohexane (gamma-cyclogeraniol) and 4.0 g of 90-95% pure 1-hydroxymethyl-2-methylene-3,3-dimethylcyclohexane.

Aufarbeitung

  1. additionAfter completion of the addition
  2. extractionWorkup of this mixture involved extraction with 150 ml ether
  3. washwashing with 10% NaCl solution
  4. customSolvent removal under reduced pressure
  5. customprovided 30 g of crude product which

Quellen und Nachweise

ORD-Eintrag
ord-94b48a7f8171497b89c43ede63450567
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04179468

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