Hydrochloric Acid → alpha-Difluoromethoxyimino-o-tolylacetonitrile

HRID 726858Notes

Reaction equation

HRID 726858 reaction equation
Cl[CH:2]([F:4])[F:3].[K].[OH:6][N:7]=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:9]#[N:10].C1OCCOCCOCCOCCOCCOC1.[OH-].[Na+].Cl>O.O1CCOCC1>[F:3][CH:2]([F:4])[O:6][N:7]=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:9]#[N:10]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 2855718-Crown-6HCID 5462222PotassiumHCID 73187596alpha-Hydroxyimino-o-tolylacetonitrile

Product 1

HCID 57050284alpha-Difluoromethoxyimino-o-tolylacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Chlorodifluoromethane is passed at 20° C. into a suspension of 18.5 g of the potassium salt of α-hydroxyimino-o-tolylacetonitrile, 1.0 g of 18-crown-6 and 185 ml of dioxane. Simultaneously a solution of 15.96 g of sodium hydroxide in 16.1 ml of water is added dropwise thereto. After subsequently stirring for 3 hours, the reaction mixture is poured onto ice-water and acidified with 2N hydrochloric acid. After extraction with ethyl acetate, the combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexane/ethyl acetate (9:1) yields α-difluoromethoxyimino-o-tolylacetonitrile in the form of a yellow liquid.

Workup

  1. additionthe reaction mixture is poured onto ice-water
  2. extractionAfter extraction with ethyl acetate
  3. washthe combined organic phases are washed with a saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5002d07dfd9c4a26a37431aeffa9d378
Source dataset
uspto-grants-1998_01
Patent number
US05710314

Reaction notes

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