Acetic Acid → 4-Oxo-1-phenylcyclohexanenitrile

HRID 76954Notes

Reaction equation

HRID 76954 reaction equation
COC([CH:5]1[CH2:10][C:9]([C:17]#[N:18])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:19])=O.C(O)(=O)C>S(=O)(=O)(O)O.O>[O:19]=[C:6]1[CH2:7][CH2:8][C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:17]#[N:18])[CH2:10][CH2:5]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 582396Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate

Product 1

HCID 912824-Oxo-1-phenylcyclohexanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

5-cyano-2-oxo-5-phenyl cyclohexane carboxylic acid methyl ester (16.1 g, 63 mmol) was dissolved in 10% sulphuric acid (218 mL) and conc. acetic acid (502 mL) and stirred for 21 h at 100° C. For work up the batch was carefully diluted with water (400 mL) with ice cooling, extracted with ethyl acetate (3×100 mL), the organic phase washed thoroughly with water (6×100 mL), saturated NaHCO3 solution (10×100 mL) and saturated NaCl solution (1×100 mL). After drying with Na2SO4 the solvent was distilled off in a vacuum.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washthe organic phase washed thoroughly with water (6×100 mL), saturated NaHCO3 solution (10×100 mL) and saturated NaCl solution (1×100 mL)
  3. dry with materialAfter drying with Na2SO4 the solvent
  4. distillationwas distilled off in a vacuum

Sources & evidence

ORD record
ord-e0defa986ba9444897ad8eb8db284e73
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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