Phenol → {2-[(2,4,4-Trimethylpentan-2-yl)peroxy]propan-2-yl}benzene

HRID 1733397

반응식

HRID 1733397 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[CH3:10][C:11]([O:18][OH:19])([CH3:17])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14].C1(O)C=CC=CC=1>>[C:11]([O:18][O:19][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:1])[CH3:3])([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:17])[CH3:10]

참가 물질

4

반응물 3

HCID 996PhenolHCID 7407Alpha-MethylstyreneHCID 798771,1,3,3-Tetramethylbutyl hydroperoxide

생성물 1

HCID 71442156{2-[(2,4,4-Trimethylpentan-2-yl)peroxy]propan-2-yl}benzene수율 81.5%

반응 조건

온도
25 °C

실험 절차

Into the 200 ml jacketed reactor described in Example II were added 18.0 grams (0.152 m) alpha-methylstyrene, 18.4 grams (0.11 m) 87.6% 1,1,3,3-tetramethylbutyl hydroperoxide and 4.6 grams (0.048 m) phenol. The mixture was stirred to obtain a clear solution and the temperature was adjusted to 20° C. To this solution was added 1.7 grams (0.011 m) of t-cumyl chloride from the addition funnel over 5 minutes while holding the temperature at 20°-21° C. The reaction was stirred 5 minutes at 21°-22° C., warmed to 25° C. and stirred 1/2 hour at 25° C., 1/2 hour at 30° C., 1/2 hour at 35° C., 11/2 hours at 40° C. and finally 1/2 hour at 45° C. At this point the t-octyl hydroperoxide had been completely consumed and the reaction was terminated by adding 50 mls of water, stirring 5 minutes, adding 10 mls of 50% NaOH, stirring another 5 minutes and separating the aqueous caustic layer. The organic layer was successively washed with 50 mls 15% NaOH, saturated NaHCO3 solution, H2O, 15% NaHSO3 solution, saturated NaHCO3 solution and water. After drying over anhydrous sodium sulfate the crude product weighed 32.6 grams and contained 72.6% cumyl t-octyl peroxide for a corrected yield of 23.7 grams and a 81.5% yield.

후처리

  1. customto obtain a clear solution
  2. customwas adjusted to 20° C
  3. customat 20°-21° C
  4. stirringThe reaction was stirred 5 minutes at 21°-22° C.
  5. stirringstirred 1/2 hour at 25° C., 1/2 hour at 30° C., 1/2 hour at 35° C.
  6. custom2 hours
  7. customat 40° C.
  8. customfinally 1/2 hour
  9. customat 45° C
  10. customAt this point the t-octyl hydroperoxide had been completely consumed
  11. customthe reaction was terminated
  12. additionby adding 50 mls of water
  13. stirringstirring 5 minutes
  14. additionadding 10 mls of 50% NaOH
  15. stirringstirring another 5 minutes
  16. customseparating the aqueous caustic layer
  17. washThe organic layer was successively washed with 50 mls 15% NaOH, saturated NaHCO3 solution, H2O, 15% NaHSO3 solution, saturated NaHCO3 solution and water
  18. dry with materialAfter drying over anhydrous sodium sulfate the crude product

출처 및 근거

ORD 기록
ord-c74188a362f84b028c5c77197529be42
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04241222

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