Catechol → 2-(2,2,2-Trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

HRID 1417231Notes

Reaction equation

HRID 1417231 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[OH-].[Na+].Cl[C:12](=[CH:17][C:18]([F:21])([F:20])[F:19])[C:13]([F:16])([F:15])[F:14]>CN(C)C=O>[F:14][C:13]([F:16])([F:15])[CH2:12][C:17]1([C:18]([F:21])([F:20])[F:19])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1

Participants

5

Reactant 3

HCID 289CatecholHCID 98152-Chloro-1,1,1,4,4,4-hexafluoro-2-buteneHCID 14798Sodium Hydroxide

Product 1

HCID 536673032-(2,2,2-Trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11 g of pyrocatechol were dissolved in 200 ml of dimethylformamide, and 18 g of 45% strength by weight aqueous sodium hydroxide solution were added. 20 g of 2-chloro-1,1,1,4,4,4-hexafluoro-2-butene were added dropwise at 75° C. to the mixture. Stirring was continued at 75° C. for 30 minutes. The mixture was then poured into 500 ml of ice-water and extracted with diethyl ether. The organic phase was washed with water, dried with magnesium sulphate and concentrated. Finally, the product was distilled under a high vacuum. The yield was 15 g (=56%) and the boiling point was 60° C. at 10 mbar. The NMR spectra showed the following characteristic absorptions: 19F-NMR: -59.0 and -84.6 ppm; 1H-NMR: 3.02 ppm.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with water
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. distillationFinally, the product was distilled under a high vacuum

Sources & evidence

ORD record
ord-40afba01b7494084b3a170280217fa80
Source dataset
uspto-grants-1999_03
Patent number
US05877195

Reaction notes

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