Sulfuric Acid → 4-Oxo-1-phenylcyclohexanenitrile

HRID 543856Notes

Reaction equation

HRID 543856 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 Preparation I, 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 percent 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. customthe procedure of Preparation I, Part c
  2. custom, respectively, and finally recrystallizing the residual solid
  3. additionfrom a mixture of ethyl acetate and hexane
  4. customthere is obtained 25.75 gm

Sources & evidence

ORD record
ord-7bb7320a5d3245b1b060501e8fcc2856
Source dataset
uspto-grants-1984_05
Patent number
US04447454

Reaction notes

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