Acetic Acid → 4-Oxo-1-phenylcyclohexanenitrile

HRID 1576199Notes

Reaction equation

HRID 1576199 reaction equation
[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH:7](C(OC)=O)[C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2].C(O)(=O)C.S(=O)(=O)(O)O>O>[C:1]([C:3]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:4][CH2:5][C:6](=[O:13])[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 582396Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate

Product 1

HCID 912824-Oxo-1-phenylcyclohexanenitrileYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 44.7 g. (0.174 mole) of methyl 5-cyano-5-phenyl-2-oxocyclohexanecarboxylate in 1200 ml. of acetic acid and 600 ml. of 10% sulfuric acid is stirred mechanically on a steam bath for about 7 hours. The mixture is then allowed to cool and diluted with water. This mixture is extracted thoroughly with benzene. The organic layer is washed successively with water, sodium bicarbonate solution and brine and evaporated to dryness. The solid residue is recrystallized from a mixture of ethyl acetate and cyclohexane to give 25.75 g. (74.2% yield) of 4-cyano-4-phenylcyclohexanone, having a melting point of 112° to 115°C.

Workup

  1. additionA mixture of 44.7 g
  2. temperatureto cool
  3. extractionThis mixture is extracted thoroughly with benzene
  4. washThe organic layer is washed successively with water, sodium bicarbonate solution and brine
  5. customevaporated to dryness
  6. customThe solid residue is recrystallized from a mixture of ethyl acetate and cyclohexane
  7. customto give 25.75 g

Sources & evidence

ORD record
ord-a908e60106c842a581bdc442b6af93cc
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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