tert-Butyl hydroperoxide → 62204-54-0

HRID 616578Notes

Reaction equation

HRID 616578 reaction equation
[OH-].[Na+].[C:3]([O:7][OH:8])([CH3:6])([CH3:5])[CH3:4].[C:9]([N:13]=[N:14][C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(Cl)[CH3:16])([CH3:12])([CH3:11])[CH3:10]>CO>[C:9]([N:13]=[N:14][C:15]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([O:8][O:7][C:3]([CH3:6])([CH3:5])[CH3:4])[CH3:16])([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 14798Sodium HydroxideHCID 2334477457908-73-3

Product 1

HCID 2334475762204-54-0Yield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 2.0 grams (.025 moles) of 50% sodium hydroxide in 20 ml. of methanol, cooled to 15° C in a 50 ml. erlenmeyer flask was added 2.77 grams (.0277 moles) of 90% t-butylhydroperoxide slowly and with rapid stirring. After the addition was complete, the reaction was stirred for 10 minutes at 10° C. To the above solution was added 4.05 grams (.02 moles) of 1-t-butylazo-1-phenyl-1-chloroethane dropwise over a 15 minute period holding the temperature at 10° C. After the addition was complete, the reaction was stirred for 30 minutes at 0°-5° C, poured into 150 ml. of ice water and extracted with pentane. The pentane solution was washed with 10% potassium hydroxide solution, water, saturated NaHCO3 solution, water, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure to leave 3.3 grams (65% yield) of crude 1-t-butylazo-1-phenyl-1-(t-butylperoxy)ethane. The infrared spectrum indicated the product was contaminated to a small extent by 1-t-butylazo -1-phenyl-1-methoxyethane which resulted from the chloro compound reacting to a small extent with the methanol solvent.

Workup

  1. additionAfter the addition
  2. customat 10° C
  3. additionAfter the addition
  4. stirringthe reaction was stirred for 30 minutes at 0°-5° C
  5. additionpoured into 150 ml
  6. extractionof ice water and extracted with pentane
  7. washThe pentane solution was washed with 10% potassium hydroxide solution, water, saturated NaHCO3 solution, water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe pentane evaporated under reduced pressure

Sources & evidence

ORD record
ord-9754487cd0ca4c1a9f5331403e47ccd6
Source dataset
uspto-grants-1978_02
Patent number
US04075199

Reaction notes

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