tert-Butyl hydroperoxide → HCID 22490916, compound

HRID 2180555Notes

Reaction equation

HRID 2180555 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:8]([CH3:16])([CH3:15])[CH2:7][CH2:6][CH2:5]2.C([O:21]O)(C)(C)C>ClCCl.[O-2].[Cr+6].[O-2].[O-2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([C:8]([CH3:15])([CH3:16])[CH2:7][CH2:6][C:5]2=[O:21])=[CH:10][C:11]=1[O:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 22490903HCID 22490903, compound

Product 1

HCID 22490916HCID 22490916, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 6-bromo-7-ethoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Compound A-3, 5.83 g, 20.6 mmol) in dichloromethane (25 mL) and tert-butyl hydroperoxide (25 mL) at room temperature was added a catalytic amount of chromium (VI) oxide. The reaction was stirred overnight. Quenched the reaction with water and followed by extraction with diethylether. The organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo. Purification by flash column chromatography (silica gel, 2% ethyl acetate/hexane) yielded the title compound as a white solid.

Workup

  1. customQuenched
  2. customthe reaction with water
  3. extractionfollowed by extraction with diethylether
  4. washThe organic layers were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (silica gel, 2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1d0c2f9eb40442ad9e09ce30d57586e1
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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