Hexafluoropropylene → HCID 19098619, compound

HRID 1975752Notes

Reaction equation

HRID 1975752 reaction equation
[C:1]([NH:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=1[Cl:13])(=[O:3])[CH3:2].[OH-].[K+].[F:16][C:17]([F:24])([F:23])[C:18]([F:22])=[C:19]([F:21])[F:20]>CN(C)C=O>[C:1]([NH:4][C:5]1[C:6]([Cl:13])=[CH:7][C:8]([O:12][C:19]([F:21])([F:20])[CH:18]([F:22])[C:17]([F:24])([F:23])[F:16])=[CH:9][C:10]=1[Cl:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8302HexafluoropropyleneHCID 14797Potassium HydroxideHCID 19384988HCID 19384988, compound

Product 1

HCID 19098619HCID 19098619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

47 g of 4-acetylamino-3,5-dichlorophenol together with 154 g of 90% potassium hydroxide solution and 130 ml of dimethylformamide are stirred in an autoclave. 75.8 g of hexafluoropropylene are then pressed into the closed autoclave. The mixture is stirred for 20 hours at 70° C. under the pressure developing in the autoclave. After cooling, the mixture is concentrated by rotary evaporation and the residue is dissolved in methylene chloride. The resultant solution is washed with water, dried over Na2SO4 and concentrated. The crude product obtained as residue is chromatographed through a column of silica gel (length: 1 m; diameter: 10 cm) eluted with an 11:1 mixture of toluene and acetone, affording 4-acetylamino-3,5-dichloro-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene in the form of pale yellow crystals (m.p.: 113°-115° C.), 26 g of which are kept for 10 hours under reflux with 110 ml of ethanol and 35.6 ml of 37% hydrochloric acid. The reaction mixture is then concentrated, diluted with ice/water and made weakly alkaline. The product is extracted from the mixture with methylene chloride. The organic extract phase is washed with water, dried over Na2SO4 and concentrated. The residue is purified by distillation, thus affording the title compound of the formula ##STR12## as a colourless liquid with a boiling point of 91°-96° C./0.001 torr.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated by rotary evaporation
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washThe resultant solution is washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product obtained as residue
  8. customis chromatographed through a column of silica gel (length: 1 m; diameter: 10 cm)
  9. washeluted with an 11:1 mixture of toluene and acetone

Sources & evidence

ORD record
ord-7157f2b73f6b49749f4e798151bf4942
Source dataset
uspto-grants-1994_02
Patent number
US05288756

Reaction notes

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