Formic Acid → 4-(4-Ethoxy-2,3-difluorophenyl)cyclohexanone

HRID 2120500Notes

Reaction equation

HRID 2120500 reaction equation
C1O[C:4]2([CH2:9][CH2:8][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[C:12]([F:19])[C:11]=3[F:20])[CH2:6][CH2:5]2)[O:3]C1.C(O)=O>C1(C)C=CC=CC=1>[F:20][C:11]1[C:12]([F:19])=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:10]=1[CH:7]1[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 220205208-(2,3-Difluoro-4-ethoxyphenyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 111611214-(4-Ethoxy-2,3-difluorophenyl)cyclohexanoneYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Crude 4-(2,3-difluoro-4-ethoxyphenyl)-cyclohexanone monoethylene acetal (50.3 mmol) obtained in Step 1 was dissolved in 200 ml of toluene, 87% formic acid (503 mmol) was added, and the solution was heated to reflux for 4 hours. The reaction solution was washed twice with 100 ml of a saturated aqueous solution of sodium hydrogen carbonate, then three times with 100 ml of water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, to form crude 4-(2,3-difluoro-4-ethoxyphenyl)-cyclohexanone (50.3 mmol).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 4 hours
  3. washThe reaction solution was washed twice with 100 ml of a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialthree times with 100 ml of water, and dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-493bf51639fe4947b892441bb96492d4
Source dataset
uspto-grants-2004_02
Patent number
US06692657B1

Reaction notes

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