Trifluoroacetic acid → Cyclohexyl trifluoroacetate
Reaction equation
[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([C:11]([OH:13])=[O:12])([F:10])([F:9])[F:8]>>[CH:1]1([O:13][C:11](=[O:12])[C:7]([F:10])([F:9])[F:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
3
Procedure
Activation of cyclohexane was also investigated in two experiments. Under anhydrous conditions, slow addition of Cu(I) dissolved in CF3CO2H to a solution of Cu(II) dissolved in CF3CO2H/C6H12 in air and gave a 17% yield of cyclohexyltrifluoroacetate. A 19.2% yield of this ester was obtained when solid Cu2O was stirred in the Cu(II) solution under a 100% O2 atmosphere. The yields are comparable even under widely varying conditions. Also, the yields are higher than for methane activation, probably due primarily to easier activation of a secondary hydrogen atom, aided by a higher solution concentration of cyclohexane (0.4M compared to about 0.01M).
Workup
- additionUnder anhydrous conditions, slow addition of Cu(I)
- dissolutiondissolved in CF3CO2H/C6H12 in air