Hydrochloric Acid → 1-(2-Fluorophenyl)-4-oxocyclohexane-1-carbonitrile

HRID 617742Notes

Reaction equation

HRID 617742 reaction equation
[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH2:8][CH:7](C(OC)=O)[C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2].Cl>O>[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH2:8][CH2:7][C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21834546Methyl 5-cyano-5-(2-fluorophenyl)-2-oxocyclohexanecarboxylate

Product 1

HCID 218345521-(2-Fluorophenyl)-4-oxocyclohexane-1-carbonitrileYield 40.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 5-cyano-5-(2-fluorophenyl)-2-oxocyclohexane-1-carboxylate (D19, 30.66 g, 0.11 mol) was stirred at reflux in c. HCl (500 ml) for 17 h, cooled, diluted with water (500 ml), and extracted with ethyl acetate. This organic portion was extracted with potassium carbonate solution, dried (Na2SO4) and evaporated to give 4-cyano-4-(2-fluorophenyl)cyclohexanone (9.58 g, 38%) as a yellow foam. The alkaline extract was re-acidified with c. HCl, and the product isolated by extraction with ethyl acetate, drying (Na2SO4) and evaporation. This gave the title compound (16.36 g, 62%) as a colourless gum.

Workup

  1. temperatureat reflux in c
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. extractionThis organic portion was extracted with potassium carbonate solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-7d9f8d759d9241bd81333fe9d41596ef
Source dataset
uspto-grants-1999_09
Patent number
US05952325

Reaction notes

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