Carbon Dioxide → 4-Oxo-1-phenylcyclohexanenitrile

HRID 1284016Notes

Reaction equation

HRID 1284016 reaction equation
[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7][C:6]([O-:9])=[C:5](C(OC)=O)[CH2:4]1)#[N:2].[Na+].Cl.C(=O)=O.[OH-].[Na+]>C(O)(=O)C.O>[C:14]1([C:3]2([C:1]#[N:2])[CH2:4][CH2:5][C:6](=[O:9])[CH2:7][CH2:8]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23711438HCID 23711438, compound

Product 1

HCID 912824-Oxo-1-phenylcyclohexanenitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a flask they were introduced successively under nitrogen atmosphere 179.7 g of sodium 4-cyano 4-phenyl 2-methoxy carbonyl cyclohex-1-enolate, 450 ml water, 450 ml acetic acid then 180 ml hydrochloric acid. It appears a milky suspension which is heated to reflux under stirring. After 5 hours heating the evolution of carbon dioxide has ceased and a green homogeneous solution is obtained. After reverting to room temperature this solution is carefully neutralized by adding a 5 N solution of sodium hydroxide while maintaining the inner temperature at about 20° by means of a iced water bath.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. customa green homogeneous solution is obtained
  4. customAfter reverting to room temperature
  5. temperaturewhile maintaining the inner temperature at about 20° by means of a iced water bath

Sources & evidence

ORD record
ord-82227f87a5294871982f8a1f0b1b3926
Source dataset
uspto-grants-1976_08
Patent number
US03978044

Reaction notes

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