tert-Butyl hydroperoxide → HCID 70374144, compound

HRID 1650036Notes

Reaction equation

HRID 1650036 reaction equation
[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[NH:28][C:27]([CH3:34])([CH3:33])[CH2:26]1)(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[NH:16][C:15]([CH3:22])([CH3:21])[CH2:14]1)=[O:11].[C:35]([O:39]O)([CH3:38])([CH3:37])C>[Mo](=O)(=O)=O.C1C2C(CCCC2)CCC1>[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[N:28]([O:39][CH:35]2[CH:38]3[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7]3)[CH2:2][CH2:1][CH2:37]2)[C:27]([CH3:34])([CH3:33])[CH2:26]1)(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:19])([CH3:20])[N:16]([O:39][CH:35]2[CH:38]3[CH:14]([CH2:13][CH2:18][CH2:17][CH2:19]3)[CH2:15][CH2:21][CH2:37]2)[C:15]([CH3:21])([CH3:22])[CH2:14]1)=[O:11]

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-tetramethylpiperdin-4-yl) sebacate, 55.0 g (0.427 mol) of 70% aqueous tert-butyl hydroperoxide, 1.5 g (0.01 mol) of molybdenum trioxide and 180 ml of decahydronaphthalene (decalin) is heated at reflux for 4.5 hours till the red color disappears. Water is collected in a Dean-Stark trap. The molybdenum trioxide is removed by filtration and the filtrate is stirred with a solution of 26 g of sodium sulfite in 500 ml of water to decompose unreacted tert-butyl hydroperoxide. The 2-phase mixture is diluted with 200 ml of ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated at reduced pressure to give an oil. Purification by flash chromatography (silica gel, 19:1 heptane:ethyl acetate) affords 28.8 g (71% yield) of the title compound as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-551efa3ac15a40abb1b26c695ec68d6e
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Reaction notes

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