Water → 4-(Trifluoromethyl)cyclohexane-1-carbaldehyde

HRID 2172236Notes

Reaction equation

HRID 2172236 reaction equation
[F:1][C:2]([F:12])([F:11])[C@@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.I(C1C=CC=CC=1C(O)=O)(=O)=O.O.C(OCC)(=O)C>CS(C)=O>[F:1][C:2]([F:11])([F:12])[CH:3]1[CH2:4][CH2:5][CH:6]([CH:9]=[O:10])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 1087942-Iodoxybenzoic acidHCID 178520944HCID 178520944, compound

Product 1

HCID 197631004-(Trifluoromethyl)cyclohexane-1-carbaldehydeYield 125.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

After dissolving [cis-4-(trifluoromethyl)cyclohexyl]methanol (2.04 g, 10.2 mmol) in dimethylsulfoxide (30 ml), 2-iodoxybenzoic acid (4.00 g, 14.3 mmol) was added thereto and stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, the insoluble matter was removed by filtration, and then the filtrate was separated into layers. The organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated to afford the title compound as a colorless oil (2.3 g, 100%).

Workup

  1. additionwas added
  2. customthe insoluble matter was removed by filtration
  3. customthe filtrate was separated into layers
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8e52f2b652e41d387388aa0b2345957
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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