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

HRID 1448545Notes

Reaction equation

HRID 1448545 reaction equation
C([CH:5]1[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])([C:11]#[N:12])[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>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:9]1([C:11]#[N:12])[CH2:8][CH2:7][C:6](=[O:20])[CH2:5][CH2:10]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanoneHCID 125955292-Carbomethoxy-4-cyano-4-(o-chlorophenyl)cyclohexanone

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-(o-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-6417167a390e4ff2b4ad4c81c02cdfff
Source dataset
uspto-grants-1979_12
Patent number
US04180584

Reaction notes

Loading…