Hydrogen Peroxide → 1,2-Epoxy-1,2,3,4-tetrahydronaphthalene

HRID 1768398Notes

Reaction equation

HRID 1768398 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1.CCCCCCCCCCCC.NC(N)=[O:25].C(=O)(O)[O-].[Na+].OO>O.ClCCl.S([O-])([O-])(=O)=O.[Mn+2]>[CH2:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]2[O:25][CH:7]2[CH2:8]1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 8182DodecaneHCID 99381,2-DihydronaphthaleneHCID 516892Sodium Bicarbonate

Product 1

HCID 921821,2-Epoxy-1,2,3,4-tetrahydronaphthaleneYield 99%

Reagents, catalysts & solvents 3

HCID 24580Manganese SulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mechanically stirred solution of 1,2-dihydronaphthalene (0.01 mol), dodecane (0.00 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 of dichloromethane at 25° C. is added 30% aqueous hydrogen peroxide (0.4 mol) in three equal portions over a period of 3 hours. After 4 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 1,2-dihydronaphthalene oxide in 99% yield with selectivity 95%.

Workup

  1. extractionAfter 4 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-cf13710ff6d84740bab154b71f156284
Source dataset
uspto-grants-2007_06
Patent number
US07235676B2

Reaction notes

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