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

HRID 462275Notes

Reaction equation

HRID 462275 reaction equation
C([CH:5]1[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)([C:11]#[N:12])[CH2:8][CH2:7][C:6]1=[O:20])(OC)=O.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:9]2([C:11]#[N:12])[CH2:8][CH2:7][C:6](=[O:20])[CH2:5][CH2:10]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture consisting of 29.8 gm (0.102 mole) of 2-carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone (prepared in Part B, above), 660 ml. glacial acetic acid, and 330 ml. 10% aqueous sulfuric acid is heated on a steam bath at about 100° C. for 24 hours. The mixture is stirred continuously. After cooling, the mixture is diluted with 1300 ml. water, and extracted with benzene. The benzene phase is recovered and washed successively with water, with aqueous sodium bicarbonate, and with brine. The benzene is then removed by evaporation under reduced pressure to give a solid residue. The solid residue is recrystallized from diethyl ether to give 12.13 gm. (82% yield) of 4-(p-chlorophenyl)-4-cyanocyclohexanone having a melting point at 94.5° to 97° C.

Workup

  1. customprepared in Part B
  2. temperatureAfter cooling
  3. additionthe mixture is diluted with 1300 ml
  4. extractionwater, and extracted with benzene
  5. customThe benzene phase is recovered
  6. washwashed successively with water, with aqueous sodium bicarbonate
  7. customThe benzene is then removed by evaporation under reduced pressure
  8. customto give a solid residue
  9. customThe solid residue is recrystallized from diethyl ether
  10. customto give 12.13 gm

Sources & evidence

ORD record
ord-4297f193c17248d99ff292ce568b9f43
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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