Formic Acid → 4-(3,4,5-Trifluorophenyl)cyclohexan-1-one

HRID 1769574Notes

Reaction equation

HRID 1769574 reaction equation
C(O)=O.C1(C)C=CC=CC=1.C1CO[C:13]2([CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=3)[CH2:15][CH2:14]2)[O:12]1>O>[F:25][C:23]1[CH:24]=[C:19]([CH:16]2[CH2:15][CH2:14][C:13](=[O:12])[CH2:18][CH2:17]2)[CH:20]=[C:21]([F:27])[C:22]=1[F:26]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 1140TolueneHCID 867484001,1-Ethylenedioxy4-(3',4',5'-trifluorophenyl)-cyclohexane

Product 1

HCID 219932844-(3,4,5-Trifluorophenyl)cyclohexan-1-oneYield 79.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Formic acid (82.7 g) and toluene (20 ml) were added to 1,1-ethylenedioxy-4-(3',4', 5'-trifluorophenyl)cyclohexane (95.02 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (500 ml), extracting with ethyl acetate (1 l), drying the organic layer over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and recrystallizing from ethanol, to obtain 4-(3',4',5'-trifluorophenyl)cyclohexanone (63.1 g). m.p. 123.5° C.

Workup

  1. temperatureby heating the mixture
  2. temperatureunder reflux
  3. extractionextracting with ethyl acetate (1 l)
  4. dry with materialdrying the organic layer over anhydrous magnesium sulfate
  5. distillationdistilling off the solvent under reduced pressure
  6. customrecrystallizing from ethanol

Sources & evidence

ORD record
ord-bf938f53a585426caee9bf0f3e47c307
Source dataset
uspto-grants-1995_01
Patent number
US05382379

Reaction notes

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