tert-Butyl hydroperoxide → HCID 70374144, compound

HRID 1590952Notes

Reaction equation

HRID 1590952 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:7][CH:6]([O:8][C:9](=[O:31])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[NH:24][C:23]([CH3:30])([CH3:29])[CH2:22]2)=[O:19])[CH2:5][C:4]([CH3:33])([CH3:32])[NH:3]1.[C:35]([O:39]O)([CH3:38])([CH3:37])C>[Mo](=O)(=O)=O.C1C2C(CCCC2)CCC1>[CH:35]1([O:39][N:24]2[C:23]([CH3:30])([CH3:29])[CH2:22][CH:21]([O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH:6]3[CH2:7][C:2]([CH3:34])([CH3:1])[N:3]([O:39][CH:35]4[CH:38]5[CH:5]([CH2:6][CH2:7][CH2:2][CH2:1]5)[CH2:4][CH2:32][CH2:37]4)[C:4]([CH3:33])([CH3:32])[CH2:5]3)=[O:31])[CH2:26][C:25]2([CH3:28])[CH3:27])[CH:38]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9][CH2:37]1

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 164282Tinuvin 770

Product 1

HCID 70374144HCID 70374144, compoundYield 141.1%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 7044DecalinSolvent

Procedure

A mixture of 25.0 g (0.052 mol) of bis(2,2,6,6-tetramethylpiperidin-4-yl)sebacate, 55.0 g (0.427 mol) of 70% aqueous t-butyl hydroperoxide, 1.5 g (0.010 mol) of molybdenum trioxide, and 180 ml of decahydronaphthalene is heated at reflux for 4.5 hours until the red color disappears. Water is collected in a Dean-Stark trap. The molybdenum trioxide is removed by filtration and the filtrate stirred with a solution of 26 g of sodium sulfite in 500 ml of water to decompose unreacted t-butyl hydroperoxide. The two-phase mixture is diluted with ethyl acetate (200 ml) and the organic layer washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated at reduced pressure to obtain an oil. Purification by flash chromatography (silica gel, 19:1 heptane: ethyl acetate) affords 28.8 g (71% yield) of the title compound, a pale yellow oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4.5 hours until the red color
  3. customWater is collected in a Dean-Stark trap
  4. customThe molybdenum trioxide is removed by filtration
  5. additionThe two-phase mixture is diluted with ethyl acetate (200 ml)
  6. washthe organic layer washed with saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated at reduced pressure
  9. customto obtain an oil
  10. customPurification by flash chromatography (silica gel, 19:1 heptane: ethyl acetate)

Sources & evidence

ORD record
ord-41fef9211da54fcc8e9b643995869085
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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