Trifluoroacetic acid → 2,5-Dihydro[1,1'-biphenyl]-4(3H)-one

HRID 1657557Notes

Reaction equation

HRID 1657557 reaction equation
[C:1]1([CH:7]2[CH2:12][CH:11](O)[CH2:10][CH2:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=[O:18]>>[C:1]1([C:7]2[CH2:12][CH2:11][C:10](=[O:18])[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21528280HCID 21528280, compound

Product 1

HCID 136810232,5-Dihydro[1,1'-biphenyl]-4(3H)-one

Procedure

The phenyl-4-hydroxycyclohexanone produced in step (2), on mixing with a strong acid such as trifluoroacetic acid at moderate (room) temperature, yields 4-phenyl-3-cyclohexen-1-one. The thus produced compound (without isolation) is reduced at the 3-position of the cyclohexane ring, (e.g., with hydrogen in the presence of a catalyst such as palladium on charcoal) to yield 4-phenylcyclohexanone.

Sources & evidence

ORD record
ord-3e7a4ed514734b87aa6533fe413640e8
Source dataset
uspto-grants-1976_06
Patent number
US03960961

Reaction notes

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