Dicumyl peroxide → Dicumyl peroxide

HRID 2049810Notes

Reaction equation

[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.C(OC(=O)C)(=[O:14])C.[O-]O.C1(C(C)C)C=CC=CC=1.[C:30]([O:39][O:40][C:41]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([CH3:43])[CH3:42])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:32])[CH3:31]>>[C:30]([O:39][O:40][C:41]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([CH3:43])[CH3:42])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:31])[CH3:32].[C@@H:1]1([C:10]([OH:9])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([OH:14])=[O:8]

Participants

Reactant 4

HCID 6641Dicumyl peroxide

HCID 7918Acetic Anhydride

HCID 641660Hexahydrophthalic anhydride, cis-

HCID 53627471Cumen hydroperoxide

Product 2

HCID 6641Dicumyl peroxide

HCID 245564cis-1,2-Cyclohexanedicarboxylic acid

Procedure

The reaction described in Example 2 was repeated with 14.7 gm (95 millimoles) cis-1,2-cyclohexanedicarboxylic anhydride substituted for the acetic anhydride. After a total reaction time of 125 minutes (at 18°±1° C.), 9.9% of the cumene hydroperoxide remained unreacted. The reaction was quenched (sodium acetate) after a total time of 245 minutes and, after recovery in a manner similar to Example 2, afforded 35.9 gm crude product which contained about 70% dicumyl peroxide. (An approximate value for dicumyl peroxide was obtained in this case because the elution of cis-1,2-cyclohexanedicarboxylic acid on the gas-liquid chromatography column partially overlapped with the dicumyl peroxide).

Workup

customThe reaction was quenched (sodium acetate) after a total time of 245 minutes
customafter recovery in a manner similar to Example 2, afforded 35.9 gm crude product which

Sources & evidence

ORD record: ord-20550b7b99494ce5a3c05aff23536c38
Source dataset: uspto-grants-1980_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04198528

Reaction notes

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