Hydrogen Peroxide → Cyclohexanol, 5-methyl-2-(2-methyloxiranyl)-, (1R,2R,5R)-

HRID 225414

Reaktionsgleichung

Reaktionsgleichung von HRID 225414
OS([O-])(=O)=O.[Na+].O.[OH-].[Na+].[CH3:10][C@H:11]1[CH2:16][C@@H:15]([OH:17])[C@H:14]([C:18]([CH3:20])=[CH2:19])[CH2:13][CH2:12]1.OO.S([O-])([O-])=[O:24].[Na+].[Na+]>OP(O)(O)=O.O.C1(C)C=CC=CC=1>[CH3:10][C@H:11]1[CH2:16][C@@H:15]([OH:17])[C@H:14]([C:18]2([CH3:20])[O:24][CH2:19]2)[CH2:13][CH2:12]1

Komponenten

9

Edukt 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 170833(-)-IsopulegolHCID 23673662Sodium bisulfate monohydrate

Produkt 1

HCID 11701113Cyclohexanol, 5-methyl-2-(2-methyloxiranyl)-, (1R,2R,5R)-Ausbeute 160,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1004Phosphoric AcidKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Into a 500 mL 4 necked flask equipped with a stirrer and a reflux condenser, NaWO4·2H2O (6.60 g, 0.02 mol), NaHSO4·H2O (6.90 g, 0.05 mol), [(Oct)3MeN]Cl (4.04 g, 0.01 mol), 85% H3PO4 (0.98 g, 0.0085 mol), toluene (77 g) and water (10 g) were charged. After adjusting pH of the solution to 4.0 with a 20% NaOH aqueous solution (5.8 g), L-isopulegol (77.1 g, 0.5 mol) was added thereto, and a 30% H2O2 aqueous solution (85 g, 0.75 mol) was added drop-wise at a temperature in a range of 35 to 40° C. for 1.5 hours with stirring. After the reaction mixture was stirred at 40° C. for further 10 hours, a 20% sodium sulfite aqueous solution (161 g, 0.26 mol) was added drop-wise to the reaction liquid at 40° C. or lower with stirring. After left for standing, an organic layer was separated, and the resulting organic layer was washed twice with water (100 g), and then the solvent was distilled off under reduced pressure to obtain a crude epoxide (83.8 g). The epoxide was distilled with a Claisen distiller to obtain 71.0 g of isopulegol epoxide (GC purity: 95.6%, boiling point: 93° C./533 Pa). Yield was 83% based on isopulegol.

Aufarbeitung

  1. additionwas added
  2. stirringAfter the reaction mixture was stirred at 40° C. for further 10 hours
  3. customto the reaction liquid at 40° C.
  4. stirringlower with stirring
  5. waitAfter left
  6. customan organic layer was separated
  7. washthe resulting organic layer was washed twice with water (100 g)
  8. distillationthe solvent was distilled off under reduced pressure
  9. customto obtain a crude epoxide (83.8 g)
  10. distillationThe epoxide was distilled with a Claisen distiller

Quellen und Nachweise

ORD-Eintrag
ord-0b38954638cb43e1a2c5dcf9e6cba5c0
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557059B2

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