Hydrogen Peroxide → alpha-Pinene oxide

HRID 1768397Notes

Reaction equation

HRID 1768397 reaction equation
[CH3:1][C:2]1[CH:7]2[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6]2)[CH2:4][CH:3]=1.CCCCCCCCCCCC.NC(N)=[O:25].C(=O)(O)[O-].[Na+].OO>O.C(#N)C.S([O-])([O-])(=O)=O.[Mn+2]>[CH3:9][C:8]1([CH3:10])[CH:7]2[C:2]3([CH3:1])[O:25][CH:3]3[CH2:4][CH:5]1[CH2:6]2

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 6654(+-)-alpha-PineneHCID 8182DodecaneHCID 516892Sodium Bicarbonate

Product 1

HCID 91508alpha-Pinene oxideYield 85%

Reagents, catalysts & solvents 3

HCID 24580Manganese SulfateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mechanically stirred solution of α-pinene (0.01 mol), dodecane (0.001 mol), urea (0.208 mol), sodium bicarbonate (0.003 mol) and manganese sulphate (0.1 mmol) in 10.0 ml of water and 30 ml acetonitrile at 25° C. is added 30% aqueous hydrogen peroxide (0.4 mol) in three equal portions over a period of 3 hours. After 6 hours the reaction mixture was extracted with 4×5 ml diethyl ether. The combined organic layer was dried over anhydrous sodium sulphate. Removal of solvent yielded α-pinene oxide in 85% yield with selectivity 93%.

Workup

  1. extractionAfter 6 hours the reaction mixture was extracted with 4×5 ml diethyl ether
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-12c538f3fa9f49458ff47f94092767e4
Source dataset
uspto-grants-2007_06
Patent number
US07235676B2

Reaction notes

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