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

HRID 37566Notes

Reaction equation

HRID 37566 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

Conditions

Temperature
75 °C

Procedure

11 g of pyrocatechol were dissolved in 200 ml of dimethylformamide, and 18 g of 45% by weight aqueous sodium hydroxide solution were added. 20 g of 2-chloro-1,1,1,4,4,4-hexafluorobut-2-ene were added dropwise to the mixture at 75° C. The reaction mixture was subsequently stirred for 30 minutes at 75° C. and then poured into 500 ml of ice-water and extracted with diethyl ether. The organic phase was washed with water, dried over magnesium sulphate and concentrated. The product was finally distilled under 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 over magnesium sulphate
  4. concentrationconcentrated
  5. distillationThe product was finally distilled under high vacuum

Sources & evidence

ORD record
ord-3d19969650f742209c7f60c95cac3d01
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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