Phenol → {2-[(2-Methylpentan-2-yl)peroxy]propan-2-yl}benzene

HRID 1733396Notes

Reaction equation

HRID 1733396 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[C:10]([O:16][OH:17])([CH2:13][CH2:14][CH3:15])([CH3:12])[CH3:11].C1(O)C=CC=CC=1>>[C:10]([O:16][O:17][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:1])[CH3:3])([CH2:13][CH2:14][CH3:15])([CH3:12])[CH3:11]

Participants

4

Reactant 3

HCID 996PhenolHCID 7407Alpha-MethylstyreneHCID 140695282-Methylpentane-2-peroxol

Product 1

HCID 53908286{2-[(2-Methylpentan-2-yl)peroxy]propan-2-yl}benzeneYield 87.8%

Procedure

Into the 200 ml jacketed reactor described in Example II were added 15.6 grams (0.13 m) alpha-methylstyrene, 15.0 grams (0.104 m) 82% t-hexyl hydroperoxide and 4.0 grams (0.043 m) phenol. The mixture was stirred to obtain a clear solution and the temperature was adjusted to 20° C. To this solution was added 1.5 grams (0.0095 m) of t-cumyl chloride from the addition funnel over 5 minutes while holding the temperature at 21°-22° C. The reaction self-exothermed to 25° C. over 10 minutes and then was stirred an additional 1/2 hour at 25° C. The reaction was then stirred 80 minutes at 35° C. and 90 minutes at 40° C. at which point the reaction was complete. The reaction was terminated by adding 25 mls of water, stirring 5 minutes, adding 5 mls of 50% NaOH, stirring another 5 minutes and separating the aqueous caustic layer. The organic layer was successively washed with 25 mls of 15% NaOH, saturated NaHCO3 solution, water, 15% NaHSO3 solution, saturated NaHCO3 solution and water. After drying with anhydrous sodium sulfate the crude product weighed 26.7 grams and contained 80.6% cumyl t-hexyl peroxide for a corrected yield of 21.5 grams and a 87.8% yield. The pure cumyl t-hexyl peroxide was isolated by fractional distillation under vacuum.

Workup

  1. customto obtain a clear solution
  2. customwas adjusted to 20° C
  3. customat 21°-22° C
  4. customThe reaction self-exothermed to 25° C. over 10 minutes
  5. stirringwas stirred an additional 1/2 hour at 25° C
  6. stirringThe reaction was then stirred 80 minutes at 35° C. and 90 minutes at 40° C. at which
  7. customThe reaction was terminated
  8. additionby adding 25 mls of water
  9. stirringstirring 5 minutes
  10. additionadding 5 mls of 50% NaOH
  11. stirringstirring another 5 minutes
  12. customseparating the aqueous caustic layer
  13. washThe organic layer was successively washed with 25 mls of 15% NaOH, saturated NaHCO3 solution, water, 15% NaHSO3 solution, saturated NaHCO3 solution and water
  14. dry with materialAfter drying with anhydrous sodium sulfate the crude product

Sources & evidence

ORD record
ord-a44e899d708d4cf3a0774fff77fa3610
Source dataset
uspto-grants-1980_12
Patent number
US04241222

Reaction notes

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