tert-Butyl hydroperoxide → HCID 20367908, compound

HRID 616581Notes

Reaction equation

HRID 616581 reaction equation
[OH-].[K+].[C:3]([O:7][OH:8])([CH3:6])([CH3:5])[CH3:4].[C:9]([N:14]=[N:15][C:16](Cl)([CH2:18][CH:19]([CH3:21])[CH3:20])[CH3:17])([CH2:12][CH3:13])([CH3:11])[CH3:10].[OH-].[Na+]>>[C:9]([N:14]=[N:15][C:16]([O:8][O:7][C:3]([CH3:6])([CH3:5])[CH3:4])([CH2:18][CH:19]([CH3:20])[CH3:21])[CH3:17])([CH2:12][CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 4

HCID 6410tert-Butyl hydroperoxide2×HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 20367907HCID 20367907, compound

Product 1

HCID 20367908HCID 20367908, compoundYield 83%

Conditions

Temperature
25 °C

Procedure

To a cooled solution of 9.1 grams (.0407 moles) of 25% potassium hydroxide solution in a 100 ml. reaction flask equipped with a magnetic stirrer, thermometer and addition funnel was added 5.2 grams (.052 moles) of 90% t-butyl hydroperoxide. The reaction mixture was stirred for 30 minutes at 25° C and then cooled to 18° C. To the above solution was added 8.06 grams (0.037 moles) of 2-t-amylazo-2-chloro-4-methylpentane dropwise over 15 minutes holding the temperature at 18°-22° C with a cold water bath. After the addition was complete, the reaction was stirred for 10 minutes at 20° C, cooled to 5° C and stirred an additional 40 minutes. A small portion of 50% sodium hydroxide was then added to react with the excess t-butyl hydroperoxide and the reaction stirred for an additional 15 minutes, poured into 150 ml. of ice cold water and the product extracted with pentane. The pentane solution was washed with ice cold water, saturated NaHCO3 solution and water. The pentane solution was dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure to leave 8.3 grams (83% yield) of crude 2-t-amylazo-2-(t-butylperoxy)-4-methylpentane.

Workup

  1. customreaction flask
  2. customequipped with a magnetic stirrer
  3. additionthermometer and addition funnel
  4. temperaturecooled to 18° C
  5. customat 18°-22° C
  6. additionAfter the addition
  7. stirringthe reaction was stirred for 10 minutes at 20° C
  8. temperaturecooled to 5° C
  9. stirringstirred an additional 40 minutes
  10. stirringthe reaction stirred for an additional 15 minutes
  11. additionpoured into 150 ml
  12. extractionof ice cold water and the product extracted with pentane
  13. washThe pentane solution was washed with ice cold water, saturated NaHCO3 solution and water
  14. dry with materialThe pentane solution was dried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. customthe pentane evaporated under reduced pressure

Sources & evidence

ORD record
ord-d88aa8c5dee54070922470485e3563c4
Source dataset
uspto-grants-1978_02
Patent number
US04075199

Reaction notes

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