Sulfuric Acid → 1-(2-Chlorophenyl)-4-oxocyclohexanecarbonitrile

HRID 462285Notes

Reaction equation

HRID 462285 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#[N:2].C(C1CC([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)(C#N)CCC1=O)(OC)=O.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:28][C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][C:24]=1[C:3]1([C:1]#[N:2])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanoneHCID 122356394-Oxocyclohexane-1-carbonitrile

Product 1

HCID 125955391-(2-Chlorophenyl)-4-oxocyclohexanecarbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Example 1, Part C, but substituting 33.4 gm. (0.115 mole) of 2-carbomethoxy-4-chlorophenyl)-4-cyanocyclohexanone (prepared in Part B, above) for the 29.8 gm. of the 2-carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone, using 730 ml. glacial acetic acid and 365 ml. 10 percent aqueous sulfuric acid instead of the 660 ml. and 330 ml., respectively, and heating for 48 hours instead of 24 hours there is obtained a residual solid that is recrystallized from a mixture of methylene chloride and technical hexane thus affording 20.54 gm. (80% yield) of 4-(o-chlorophenyl)-4-cyanocyclohexanone having a melting point at 106° to 108° C.

Workup

  1. temperature, respectively, and heating for 48 hours instead of 24 hours there
  2. customis obtained a residual solid
  3. customthat is recrystallized from a mixture of methylene chloride and technical hexane
  4. customthus affording 20.54 gm

Sources & evidence

ORD record
ord-520fd77326694c4186eb7f608c6e6760
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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