2-Isopropylphenol → Cyclohexanol

HRID 1605144Notes

Reaction equation

HRID 1605144 reaction equation
[C:1]1(C(C)C)[C:2]([OH:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[O-:11]O.[O-]O.C1(C(C)C)C=CC=CC=1>C1CCCCC1>[CH:2]1([O:7][OH:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:1]1.[CH:2]1([OH:7])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:1]1.[C:2]1(=[O:7])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:1]1

Participants

7

Reactant 3

HCID 69432-Isopropylphenol2×HCID 18500Perhydroxyl radicalHCID 53627471Cumen hydroperoxide2×

Product 3

HCID 7966CyclohexanolHCID 7967CyclohexanoneHCID 69835Cyclohexyl hydroperoxide

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

A run was carried out in exactly the same manner as Run 10, except that the tertiary alcohol was cumenol and the tertiary hydroperoxide was cumene hydroperoxide. The mole ratio of cumenol to cyclohexane was 0.329:1 and the mole ratio of cumene hydroperoxide to cyclohexane was 0.086:1. A cyclohexyl hydroperoxide yield of 56 mole per cent, a cyclohexanol yield of 20 mole per cent, a cyclohexanone yield of 11 mole per cent and a residue of 13 mole per cent was obtained at a conversion level of 8.1 mole per cent and a per cent conversion rate of 5.8 per cent per hour. This run demonstrates that other tertiary alcohols and hydroperoxides are effective in the process of this invention.

Sources & evidence

ORD record
ord-4947925abe8c48258f5e3fe07f8b5fd3
Source dataset
uspto-grants-1976_04
Patent number
US03949003

Reaction notes

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