Trifluoroacetic acid → Cyclohexyl trifluoroacetate

HRID 1081450Notes

Reaction equation

HRID 1081450 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]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 8078Cyclohexane

Product 1

HCID 519124Cyclohexyl trifluoroacetateYield 17%

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

  1. additionUnder anhydrous conditions, slow addition of Cu(I)
  2. dissolutiondissolved in CF3CO2H/C6H12 in air

Sources & evidence

ORD record
ord-49c44a602d1348b38aa356cf8e63cceb
Source dataset
uspto-grants-1996_12
Patent number
US05585515

Reaction notes

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