tert-Butyl hydroperoxide → 6-Bromo-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 853190Notes

Reaction equation

HRID 853190 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C([O:18]O)(C)(C)C>ClCCl.O.[O-2].[Cr+6].[O-2].[O-2]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][CH:3]=1)[C:6](=[O:18])[CH2:7][CH2:8][C:9]2([CH3:13])[CH3:12]

Participants

6

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 105379407-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene2×

Product 1

HCID 118319356-Bromo-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-oneYield 79%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound 2, 1.1 g, 4.62 mmol) in 10 mL of dichloromethane was added chromium (VI) oxide (72 mg, 0.46 mmol) and 5 mL of tert-butyl hydroperoxide solution (TBHP). After stirring at room temperature for 8 h, the mixture was diluted with water (20 mL), extracted with diethyl ether (3×10 mL), washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (90:10 hexane/ethyl acetate) yielded the title compound (920 mg, 79% yield) as a white solid:

Workup

  1. extractionextracted with diethyl ether (3×10 mL)
  2. washwashed with brine (1×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customPurification by flash chromatography (90:10 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e9023d68eed54563953ee12f34e64539
Source dataset
uspto-grants-2007_08
Patent number
US07253319B2

Reaction notes

Loading…