tert-Butyl hydroperoxide → HCID 22490907, compound

HRID 2180601Notes

Reaction equation

HRID 2180601 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:15])[C:11]=1[O:12][CH2:13][CH3:14])[C:8]([CH3:17])([CH3:16])[CH2:7][CH2:6][CH2:5]2.C([O:22]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]([CH3:16])([CH3:17])[CH2:7][CH2:6][C:5]2=[O:22])=[C:10]([Cl:15])[C:11]=1[O:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 22490830HCID 22490830, compound

Product 1

HCID 22490907HCID 22490907, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-8-chloro-7-ethoxy-1,1-dimethyl-1,2,3,4 tetrahydronaphthalene (Compound A-118, 4.1 g, 12.93 mmol) in dichloromethane (20 mL) and tert-butyl hydroperoxide (20 mL) at room temperature was added a catalytic amount of chromium (VI) oxide. The reaction was stirred overnight. Quenched with the reaction with water followed by extraction with ether. 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 with the reaction with water
  2. extractionfollowed by extraction with ether
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica gel, 2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-34374f4a311d4f4f9af2b62cda5511e8
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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