Acetone → Cyclohexanone

HRID 2085612Notes

Reaction equation

HRID 2085612 reaction equation
[C:1]1([CH:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)CCC[CH2:12][CH2:11]1.CC(C)=[O:24]>>[C:1]1(=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:10][CH2:11][CH2:12][CH2:8]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 7406CumeneHCID 13229Cyclohexylbenzene2×

Product 2

HCID 7967CyclohexanoneHCID 519199Cyclododecylbenzene

Procedure

Both the preparation of the starting material prepared by alkylation, e.g. cumene, cyclohexylbenzene (in the Hock process, cyclohexylbenzene gives not acetone but cyclohexanone) and cyclododecylbenzene (in the Hock process, cyclododecylbenzene gives cyclododecanone), and the acid-catalysed cleavage and rearrangement to phenol which follow the oxidation step generally proceed with high selectivity to give high yields.

Workup

  1. customBoth the preparation of the starting material

Sources & evidence

ORD record
ord-b0fd436155b24925881a316335879af3
Source dataset
uspto-grants-2004_04
Patent number
US06720462B2

Reaction notes

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