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

HRID 1358903Notes

Reaction equation

HRID 1358903 reaction equation
C1(C)C=CC=CC=1.C1O[C:11]2([CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[CH2:13][CH2:12]2)[O:10]C1.C(O)=O>O>[F:23][C:21]1[CH:22]=[C:17]([CH:14]2[CH2:13][CH2:12][C:11](=[O:10])[CH2:16][CH2:15]2)[CH:18]=[C:19]([F:24])[CH:20]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 1140TolueneHCID 206101618-(3,5-Difluorophenyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 177905164-(3,5-Difluorophenyl)cyclohexan-1-oneYield 103.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of toluene was added 31 g (0.12 mol) of 4-(3,5-difluorophenyl)cyclohexanone monoethylene ketal obtained above and 76 g (1.7 mol) of formic acid, and the mixture was refluxed for 4 hours. The reaction solution was successively with water, a saturated aqueous sodium carbonate and water, dried over magnesium sulfate, and then the solvent was distilled off to afford 26 g of 4-(3,5-difluorophenyl)cyclohexanone.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. dry with materiala saturated aqueous sodium carbonate and water, dried over magnesium sulfate
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-ba2d2734853346549731ca6397c247cd
Source dataset
uspto-grants-2003_07
Patent number
US06599590B2

Reaction notes

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