tert-Butyl hydroperoxide → HCID 54246713, compound

HRID 1650028Notes

Reaction equation

HRID 1650028 reaction equation
[C:1]([O:22][CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]1)(=[O:21])[C:2]1[CH:20]=[CH:19][CH:18]=[C:4]([C:5]([O:7][CH:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]2)=[O:6])[CH:3]=1.[C:33]([O:37]O)([CH3:36])([CH3:35])C>[Mo](=O)(=O)=O.C(C1C=CC=CC=1)C>[C:5]([O:7][CH:8]1[CH2:9][C:10]([CH3:17])([CH3:16])[N:11]([O:37][CH:33]([CH3:36])[C:35]2[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=2)[C:12]([CH3:14])([CH3:15])[CH2:13]1)(=[O:6])[C:4]1[CH:18]=[CH:19][CH:20]=[C:2]([C:1]([O:22][CH:23]2[CH2:24][C:25]([CH3:32])([CH3:31])[N:26]([O:37][CH:33]([CH3:36])[C:35]3[CH:19]=[CH:20][CH:2]=[CH:3][CH:4]=3)[C:27]([CH3:30])([CH3:29])[CH2:28]2)=[O:21])[CH:3]=1

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 53929497HCID 53929497, compound

Product 1

HCID 54246713HCID 54246713, compoundYield 129.1%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 7500EthylbenzeneSolvent

Procedure

a mixture of 40.0 g (90.0 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) isophthalate, 2.0 g of molybdenum trioxide, and 250 ml of ethylbenzene is heated to 110° C. t-Butyl hydroperoxide (70%, 69.5 g, 540 mmol) is added dropwise over a 45 min. period. The reaction mixture turns red during the addition. Water is removed by azeotropic distillation. The mixture is refluxed for 4 hours after the addition is complete. The catalyst is filtered, and the filtrate is evaporated to obtain a yellow oil. A Kugelrohr distillation (110° C., 0.1 mm Hg) is performed to remove volatile by-products. The residue, a viscous oil, is dissolved in hexane and passed through silica gel. Evaporation yields a crude solid which is recrystallized from ethanol to yield 39.8 g (65% yield) of the title compound, a white powder, m.p. 118°-34° C.

Workup

  1. additionis added dropwise over a 45 min. period
  2. additionThe reaction mixture turns red during the addition
  3. customWater is removed by azeotropic distillation
  4. temperatureThe mixture is refluxed for 4 hours
  5. additionafter the addition
  6. filtrationThe catalyst is filtered
  7. customthe filtrate is evaporated
  8. customto obtain a yellow oil
  9. distillationA Kugelrohr distillation (110° C., 0.1 mm Hg)
  10. customto remove volatile by-products
  11. dissolutionThe residue, a viscous oil, is dissolved in hexane
  12. customEvaporation
  13. customyields a crude solid which
  14. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-2221471201d24294adefa9ba8a6e3f3d
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Reaction notes

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