Hydrochloric Acid → 1-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrile

HRID 2370292Notes

Reaction equation

HRID 2370292 reaction equation
COC([CH:5]1[CH2:10][C:9]([C:18]#[N:19])([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:20])=O.Cl>C(O)C>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2([C:18]#[N:19])[CH2:8][CH2:7][C:6](=[O:20])[CH2:5][CH2:10]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12230235Methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate

Product 1

HCID 918051-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrileYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

102.5 g of crude 5-Cyano-5-(4-fluoro-phenyl)-2-oxo-cyclohexanecarboxylic acid methyl ester (72) were dissolved in 680 mL of ethanol. 170 mL of conc. hydrochloric acid were added and the reaction mixture was refluxed for 40 h. The mixture was evaporated to dryness, the residue was taken up in water and extracted with dichloromethane. The combined organic layers were extracted with brine, dried over sodium sulfate and evaporated to dryness. The crude product was purified by silica gel chromatography to give 50.4 g of the desired product. Rt=1.26 min (Method C). Detected mass: 218.2 (M+H+).

Workup

  1. temperaturethe reaction mixture was refluxed for 40 h
  2. customThe mixture was evaporated to dryness
  3. extractionextracted with dichloromethane
  4. extractionThe combined organic layers were extracted with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c0c07b118bb34b208e5bd5f78012a480
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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