Sulfuric Acid → 4-Oxo-1-(p-tolyl)cyclohexanecarbonitrile

HRID 1448548Notes

Reaction equation

HRID 1448548 reaction equation
C([CH:5]1[CH2:10][C:9]([C:18]#[N:19])([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:20])(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:18]([C:9]1([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[CH2:10][CH2:5][C:6](=[O:20])[CH2:7][CH2:8]1)#[N:19]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanoneHCID 125955282-Carbomethoxy-4-cyano-4-(p-tolyl)cyclohexanone

Product 1

HCID 125955384-Oxo-1-(p-tolyl)cyclohexanecarbonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Example 1, Part C, but substituting 39.3 gm. (0.145 mole) of 2-carbomethoxy-4-cyano-4-(p-tolyl)cyclohexanone (prepared in Part B, above) for the 29.8 gm. of the 2-carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone and using 960 ml. glacial acetic acid and 480 ml. of 10 percent aqueous sulfuric acid instead of the 660 ml. and 330 ml., respectively, there is obtained after recrystallization from a mixture of diethyl ether and petroleum ether 22.84 gm. (74% yield) of 4-cyano-4-(p-tolyl)cyclohexanone having a melting range at 79° to 82° C.

Workup

  1. custom, respectively, there is obtained
  2. customafter recrystallization
  3. additionfrom a mixture of diethyl ether and petroleum ether 22.84 gm

Sources & evidence

ORD record
ord-f0ef8c4e71c44b96bf15024f09733eab
Source dataset
uspto-grants-1979_12
Patent number
US04180584

Reaction notes

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