Methallyl alcohol → HCID 22404804, compound

HRID 440666Notes

Reaction equation

HRID 440666 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].[CH2:11]([OH:15])[C:12](=[CH2:14])[CH3:13].[OH-].[K+]>CS(C)=O>[F:10][C:6]1[C:3]([C:4]#[N:5])=[C:2]([O:15][CH2:11][C:12]([CH3:14])=[CH2:13])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10557Methallyl alcoholHCID 14797Potassium HydroxideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 22404804HCID 22404804, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a flask were placed 250.0 g (1.80 moles) of 2,6-difluorobenzonitrile, 129.8 g of (1.80 moles) of methallyl alcohol, and 1500 mL of dimethyl sulfoxide. This mixture was stirred vigorously while 124.76 g (1.89 moles) of 85% powdered potassium hydroxide was added in portions. This addition required 2 hours during which the temperature was maintained below 45° C. The reaction mixture was stirred at ambient temperature for approximately 21 hours. At the conclusion of this period the mixture was poured into 4 L of an ice/water mixture. This mixture was divided into two equal portions, and each was extracted twice with 1 L of ethyl acetate. The extracts were combined and washed twice with a saturated aqueous solution of sodium chloride. The extracts were dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving 302.7 g of 6-fluoro-2-(2-methyl-2-propen-1-yloxy)benzonitrile as a residue. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customIn a flask were placed
  2. additionwas added in portions
  3. additionThis addition required 2 hours during which the temperature
  4. temperaturewas maintained below 45° C
  5. stirringThe reaction mixture was stirred at ambient temperature for approximately 21 hours
  6. extractioneach was extracted twice with 1 L of ethyl acetate
  7. washwashed twice with a saturated aqueous solution of sodium chloride
  8. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d77c1dafbf4648d880d7f839a32722d0
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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