Trifluoroacetic acid → Cyclohexyl trifluoroacetate

HRID 1081451Notes

Reaction equation

HRID 1081451 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[F:7][C:8]([F:13])([F:12])[C:9]([OH:11])=[O:10]>[Cu]>[CH:1]1([O:11][C:9](=[O:10])[C:8]([F:13])([F:12])[F:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 8079Cyclohexene

Product 1

HCID 519124Cyclohexyl trifluoroacetate

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

Both experiments with copper metal deposited the white precipitate. During the course of the second experiment, solution samples were taken for analysis. Cyclohexene was found to be the major reaction product (ester/olefin=0.2) which slowly reacted with trifluoroacetic acid to form cyclohexyltrifluoroacetate. Thus, elimination of cyclohexene from a cyclohexyl-copper complex is the predominant reaction pathway under our conditions.

Sources & evidence

ORD record
ord-1e4f4649467045e5a0e4cfff596798bf
Source dataset
uspto-grants-1996_12
Patent number
US05585515

Reaction notes

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