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

HRID 1576202Notes

Reaction equation

HRID 1576202 reaction equation
[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[CH2:8][CH:7](C(OC)=O)[C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2].C(O)(=O)C.S(=O)(=O)(O)O>O>[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[CH2:8][CH2:7][C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 13345275Methyl 5-cyano-5-(3,4-dimethoxyphenyl)-2-oxocyclohexanecarboxylate

Product 1

HCID 749913Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-Yield 67.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 29 g. (0.0915 mole) of methyl 5-cyano-5-(3,4-dimethoxyphenyl)-2-oxocyclohexanecarboxylate (prepared in Example 10) in 600 ml. of acetic acid and 300 ml. of 10% sulfuric acid is stirred mechanically on a steam bath for about 24 hours. The mixture is then allowed to cool and diluted with water. This mixture is extracted thoroughly with benzene. The organic layer is successively washed with water, sodium bicarbonate solution and brine and evaporated to dryness. The solid residue is recrystallized from a mixture of ethyl acetate and cyclohexanone to give 15.96 g. (67.3% yield) of 4-cyano-4-(3,4-dimethoxyphenyl)cyclohexanone, having a melting point of 112.5° to 114.5°C.

Workup

  1. additionA mixture of 29 g
  2. temperatureto cool
  3. extractionThis mixture is extracted thoroughly with benzene
  4. washThe organic layer is successively washed with water, sodium bicarbonate solution and brine
  5. customevaporated to dryness
  6. customThe solid residue is recrystallized from a mixture of ethyl acetate and cyclohexanone
  7. customto give 15.96 g

Sources & evidence

ORD record
ord-78769ac844334ea5926ad36ca3b76efb
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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