Acetic Acid → 1-(4-Chlorophenyl)-4-oxocyclohexanecarbonitrile

HRID 1576200Notes

Reaction equation

HRID 1576200 reaction equation
[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][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:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=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 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone

Product 1

HCID 122302381-(4-Chlorophenyl)-4-oxocyclohexanecarbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 29.8 g. (0.102 mole) of methyl 5-cyano-5-(4-chlorophenyl)-2-oxocyclohexanecarboxylate (prepared in Example 7) in 660 ml. of acetic acid and 330 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 washed successively with water, sodium bicarbonate solution and brine and evaporated to dryness. The solid residue is recrystallized from ether to give 19.49 g. (82% yield) of 4-cyano-4-(4-chlorophenyl)cyclohexanone, having a melting point of 94.5° to 97°C.

Workup

  1. additionA mixture of 29.8 g
  2. temperatureto cool
  3. extractionThis mixture is extracted thoroughly with benzene
  4. washThe organic layer is washed successively with water, sodium bicarbonate solution and brine
  5. customevaporated to dryness
  6. customThe solid residue is recrystallized from ether
  7. customto give 19.49 g

Sources & evidence

ORD record
ord-0f1876c50e4744a7893575c4349be497
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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