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

HRID 45184

Reaction equation

HRID 45184 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 62.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

101.5 g of 5-Cyano-5-(4-fluoro-phenyl)-2-oxo-cyclohexanecarboxylic acid methyl ester (11) were dissolved in 680 mL of ethanol and 171 mL of concentrated aqueous hydrochloric acid were added. The mixture was heated to reflux for 40 h, then evaporated. The residue was taken up in water and extracted with dichloromethane. The organic layer was washed with brine, dried over magnesium sulphate and evaporated to give 95.2 g of crude product, that was purified by silica gel filtration (heptanes:ethyl acetate) to yield 50.4 g of the desired product 12. Rt=1.26 min (Method 1). Detected mass: 218.2 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 40 h
  3. customevaporated
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customto give 95.2 g of crude product, that
  9. filtrationwas purified by silica gel filtration (heptanes:ethyl acetate)

Sources & evidence

ORD record
ord-73d1812c7d0141128be68c792624f4f6
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Linked notes

Loading…