Acetic Acid → 4-Oxo-1-phenylcyclohexanenitrile

HRID 1948588Notes

Reaction equation

HRID 1948588 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.O>OS(O)(=O)=O>[C:17]([C:9]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][C:6](=[O:19])[CH2:5][CH2:10]1)#[N:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 582396Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate

Product 1

HCID 912824-Oxo-1-phenylcyclohexanenitrile

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

5-cyano-2-oxo-5-phenylcyclohexanecarboxylic acid methyl ester (7.71 g, 0.03 mole) was dissolved in 10 percent H2SO4 and conc. acetic acid (240 ml). The reaction mixture was stirred for 24 hours at 100° C. The course of the reaction was followed by thin layer chromatography. The reaction mixture was worked up by dilution with water (400 ml) while cooling in ice and extracted with ethyl acetate (3×100 ml). The organic phase was then thoroughly washed with water (6×100 ml), saturated sodium hydrogen carbonate solution (10×100 ml) and saturated sodium chloride solution (1×100 ml). After drying the organic phase over Na2SO4, the solvent was distilled off on a rotary evaporator. The desired product was obtained in a yield of 5.46 g (92%) with a melting point of 106°-107° C.

Workup

  1. temperaturewhile cooling in ice
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe organic phase was then thoroughly washed with water (6×100 ml), saturated sodium hydrogen carbonate solution (10×100 ml) and saturated sodium chloride solution (1×100 ml)
  4. dry with materialAfter drying the organic phase over Na2SO4
  5. distillationthe solvent was distilled off on a rotary evaporator

Sources & evidence

ORD record
ord-f680d1c1c33643a68885e84171ea31d4
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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