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

HRID 1576201Notes

Reaction equation

HRID 1576201 reaction equation
[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][C:17]([F: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]([F: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 12230235Methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate

Product 1

HCID 918051-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33.9 g. (0.123 mole) of methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate (prepared in Example 8) in 900 ml. of acetic acid and 450 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 16.32 g. (75% yield) of 4-cyano-4-(4-fluorophenyl)cyclohexanone, having a melting point of 84° to 88°C.

Workup

  1. additionA mixture of 33.9 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 16.32 g

Sources & evidence

ORD record
ord-667e3611fafa4bd7a76d3b38d249be4f
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

Loading…