Sulfuric Acid → Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-

HRID 462280Notes

Reaction equation

HRID 462280 reaction equation
C([CH:5]1[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)([C:11]#[N:12])[CH2:8][CH2:7][C:6]1=[O:23])(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:11]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH2:10][CH2:5][C:6](=[O:23])[CH2:7][CH2:8]1)#[N:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanoneHCID 13345275Methyl 5-cyano-5-(3,4-dimethoxyphenyl)-2-oxocyclohexanecarboxylate

Product 1

HCID 749913Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-Yield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the same procedure described in Example 1, Part C, but substituting 29.0 gm. (0.0915 mole) of 2-carbomethoxy-4-(3,4-dimethoxyphenyl)-4-cyanocyclohexanone (prepared in Part B, above) for the 29.8 gm. of 2-carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone, using 600 ml. acetic acid and 300 ml. 10 percent aqueous sulfuric acid instead of the 660 ml. and 330 ml., respectively, heating on the steam bath for 48 hours instead of 24 hours, and recrystallizing from a mixture of ethyl acetate and hexane instead of diethyl ether, there is obtained 16.83 gm. (67% yield) of the desired 4-cyano-4-(3,4-dimethoxyphenyl)cyclohexanone which has a melting point at 112.5° to 114.5° C.

Workup

  1. temperature, respectively, heating on the steam bath for 48 hours instead of 24 hours
  2. customrecrystallizing from a mixture of ethyl acetate and hexane instead of diethyl ether
  3. customthere is obtained 16.83 gm

Sources & evidence

ORD record
ord-cb3c0a0daa704d249c77ad9889afe208
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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