Hydrogen Peroxide → Cumen hydroperoxide
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].OO.C(Cl)(C1C=CC=CC=1)(C)C.C([O:31][O:32]C(C1C=CC=CC=1)(C)C)(C1C=CC=CC=1)(C)C>>[O-:31][OH:32].[C:4]1([CH:2]([CH3:3])[CH3:1])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Conditions
- Temperature
- 30 °C
Procedure
Into a 250 ml round bottom flask equipped with a magnetic stirrer, condenser, thermometer and addition funnel were added 59.0 grams (B 0.05 m) α-methylstyrene and 9.8 grams (0.2 m) of 70% H2O2. The flask was immersed in a 25° C. water bath and the temperature allowed to come to 23° C. Then with rapid stirring, 6.2 grams (0.14 m) of cumyl chloride were added over 5 minutes. The reaction mixture was stirred vigorously for 35 minutes at 25° C.±2° C., the reaction temperature raised to 30° C. and stirred 1 hour at 30° C.±2° C., the reaction temperature raised to 35° C. and the reaction mixture stirred an additional hour at 35° C.±2° C., the reaction temperature raised to 40° C. and the reaction mixture stirred 1 hour at 40° C.± 2° C. At this point there was essentially no dicumyl peroxide formed and about 5% cumene hydroperoxide formed. The reaction mixture was allowed to stand at room temperature over the weekend and then stirred an additional 2 hours at room temperature. The gas chromatography scans indicated there was still less than 1% dicumyl peroxide present and about 5% cumene hydroperoxide present. The reaction mixture was stirred with 15% NaOH, the organic layer separated and discarded in the organic waste bottle since it contained essentially no dicumyl peroxide.
Workup
- customInto a 250 ml round bottom flask equipped with a magnetic stirrer, condenser
- additionthermometer and addition funnel
- customwas immersed in a 25° C.
- customto come to 23° C
- stirringstirred 1 hour at 30° C.±2° C.
- temperaturethe reaction temperature raised to 35° C.
- stirringthe reaction mixture stirred an additional hour at 35° C.±2° C.
- temperaturethe reaction temperature raised to 40° C.
- stirringthe reaction mixture stirred 1 hour at 40° C.± 2° C
- customformed
Sources & evidence
- ORD record
- ord-f27a7f5f05b54714b18702cef335617a
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04243821
Reaction notes
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