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tert-Butyl hydroperoxide → HCID 53631979, compound

HRID 1650022
Notes
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Reaction equation

HRID 1650022 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[C:3](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:4]([O:6][CH:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]([CH3:16])([CH3:15])[CH2:8]1)=[O:5].[C:33]([O:37]O)([CH3:36])([CH3:35])C>[Mo](=O)(=O)=O.C1CCCCC1>[C:4]([O:6][CH:7]1[CH2:8][C:9]([CH3:16])([CH3:15])[N:10]([O:37][CH:33]2[CH2:36][CH2:17][CH2:3][CH2:4][CH2:35]2)[C:11]([CH3:13])([CH3:14])[CH2:12]1)(=[O:5])[C:3]1[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:1]([O:22][CH:23]1[CH2:24][C:25]([CH3:32])([CH3:31])[N:26]([O:37][CH:33]2[CH2:36][CH2:20][CH2:2][CH2:1][CH2:35]2)[C:27]([CH3:30])([CH3:29])[CH2:28]1)=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxide3×HCID 1513129Bis(2,2,6,6-tetramethyl-4-piperidinyl) phthalate

Product 1

HCID 53631979HCID 53631979, compoundYield 143.3%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
81 °C

Procedure

A mixture of 30.0 grams (67.5 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) phthalate, 27.5 grams (214 mmol) of 70% aqueous tert-butyl hydroperoxide, 2.0 grams of molybdenum trioxide and 200 ml of cyclohexane is heated to reflux at 81° C. Water is collected in a Dean-Stark trap. After 75 minutes, the reaction mixture is red. Another portion of tert-butyl hydroperoxide (42.5 grams of 70% aqueous solution, 330 mmol) is added over 30 minutes. After additional water is collected in the trap, the reaction mixture is transferred to a Fischer-Porter bottle and heated at 140° C. for 4.5 hours. The nearly colorless reaction mixture is treated with 6.9 grams (69 mmol) of 90% aqueous tert-butyl hydroperoxide and heated at 140° C. for 90 minutes to remove the last traces of pink color. The reaction mixture is cooled, filtered and stirred with a solution of 43 grams of sodium sulfite in 530 ml of water for 2 hours. Methylene chloride (600 ml) is added and the organic layer is separated, dried over anhydrous magnesium sulfate and concentrated to a crude solid. Purification (Waters Prep. 500A HPLC, 25:1 heptane:ethyl acetate) affords 31.0 grams (72% yield) of the title compound as a white solid, melting at 149°-151° C.

Workup

  1. temperatureis heated
  2. customWater is collected in a Dean-Stark trap
  3. customAfter additional water is collected in the trap
  4. temperatureheated at 140° C. for 4.5 hours
  5. temperatureheated at 140° C. for 90 minutes
  6. customto remove the last traces of pink color
  7. temperatureThe reaction mixture is cooled
  8. filtrationfiltered
  9. additionMethylene chloride (600 ml) is added
  10. customthe organic layer is separated
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated to a crude solid
  13. customPurification (Waters Prep. 500A HPLC, 25:1 heptane:ethyl acetate)

Sources & evidence

ORD record
ord-47f5c113706c406dad40daa7e33ad063
Source dataset
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04921962

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes