Cyclohexanol → HCID 13715552, compound

HRID 65457Notes

Reaction equation

HRID 65457 reaction equation
F[C:2]1[C:7]([C:8]#[N:9])=[C:6]([F:10])[C:5]([C:11]#[N:12])=[C:4]([F:13])[C:3]=1[F:14].[F-].[K+].[CH:17]1([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(#N)C>[F:10][C:6]1[C:5]([C:11]#[N:12])=[C:4]([F:13])[C:3]([F:14])=[C:2]([O:23][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 522689Potassium FluorideHCID 608182Tetrafluoroisophthalonitrile

Product 1

HCID 13715552HCID 13715552, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 5.0 g amount of tetrafluoroisophthalonitrile and 2.18 g of potassium fluoride were dissolved in 25 ml of acetonitrile, and 3.83 g of cyclohexanol was then dropwise added to the mixture. After the dropwise addition, the mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered, the filtrate was concentrated in vacuo, and the concentrated liquid was poured to 50 ml of water. The resultant mixture was extracted with carbon tetrachloride. After washing with water, the extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off. Thus, 6.2 g (88% yield) of the desired compound No. 47 was obtained.

Workup

  1. additionAfter the dropwise addition
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionthe concentrated liquid was poured to 50 ml of water
  5. extractionThe resultant mixture was extracted with carbon tetrachloride
  6. washAfter washing with water
  7. dry with materialthe extract was dried with anhydrous magnesium sulfate
  8. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-3690301506f843f981b12a6e1b9e51f8
Source dataset
uspto-grants-1986_09
Patent number
US04614742

Reaction notes

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