Sulfuric Acid → 4-Oxo-1-phenylcyclohexanenitrile

HRID 462291Notes

Reaction equation

HRID 462291 reaction equation
C([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])(OC)=O.C(C1CC(C2C=CC(Cl)=CC=2)(C#N)CCC1=O)(OC)=O.S(=O)(=O)(O)O>C(O)(=O)C>[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 1118Sulfuric AcidHCID 582396Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylateHCID 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone

Product 1

HCID 912824-Oxo-1-phenylcyclohexanenitrileYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Example 1, Part C, but substituting 44.7 gm. (0.174 mole) of 2-carbomethoxy-4-cyano-4-phenylcyclohexanone (prepared as in Part B, above) for the 29.8 gm. of the 2-carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone and using 1200 ml. of the glacial acetic acid, and 600 ml. of the 10% aqueous sulfuric acid instead of the 660 ml. and the 330 ml., respectively, and finally recrystallizing the residual solid from a mixture of ethyl acetate and hexane, there is obtained 25.75 gm. (75% yield) of the desired 4-cyano-4-phenylcyclohexanone having a melting range from 112° to 115.5° C.

Workup

  1. custom, respectively, and finally recrystallizing the residual solid
  2. additionfrom a mixture of ethyl acetate and hexane
  3. customthere is obtained 25.75 gm

Sources & evidence

ORD record
ord-e6b1e0cb0c744c92806f9050379a5b54
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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