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

HRID 462278

Reaction equation

HRID 462278 reaction equation
C([CH:5]1[CH2:10][C:9]([C:18]#[N:19])([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:20])(OC)=O.S(=O)(=O)(O)O>C(O)(=O)C>[C:18]([C:9]1([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH2:10][CH2:5][C:6](=[O:20])[CH2:7][CH2:8]1)#[N:19]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12230235Methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate

Product 1

HCID 918051-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture consisting of 33.9 gm. (0.123 mole) of 2-carbomethoxy-4-cyano-4-(p-fluorophenyl)cyclohexanone (prepared in Part B, above), 900 ml. glacial acetic acid, and 450 ml. 10% aqueous sulfuric acid is heated with stirring on a steam bath for 24 hours. After allowing the reaction mixture to cool, it is diluted with 2000 ml. water and extracted thoroughly with benzene. The benzene extracts are combined and washed successively with water, with aqueous sodium bicarbonate, and finally with brine. The benzene is then removed by evaporation under reduced pressure, and the solid residue thus obtained is recrystallized from diethyl ether to afford 16.23 gm. (67% yield) of 4-cyano-4-(p-fluorophenyl)cyclohexanone having a melting point at 84° to 88° C.

Workup

  1. temperatureto cool
  2. additionit is diluted with 2000 ml
  3. extractionwater and extracted thoroughly with benzene
  4. washwashed successively with water, with aqueous sodium bicarbonate
  5. customThe benzene is then removed by evaporation under reduced pressure
  6. customthe solid residue thus obtained
  7. customis recrystallized from diethyl ether
  8. customto afford 16.23 gm

Sources & evidence

ORD record
ord-4d7e11105d8f47409fb7e8b110241c34
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Linked notes

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