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

HRID 1741025Notes

Reaction equation

HRID 1741025 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 (D2, 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 washed 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 wash 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. washThis organic portion was washed with potassium carbonate solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-23ab640edbbb457ca344761f1ec00bda
Source dataset
uspto-grants-1999_10
Patent number
US05972979

Reaction notes

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