m-Chloroperbenzoic acid → 2-(1-Chloro-2,2,2-trifluoroethyl)-2-(trifluoromethyl)-5-hydroxy-1,3-benzodioxole

HRID 37582Notes

Reaction equation

HRID 37582 reaction equation
[Cl:1][CH:2]([C:7]1([C:18]([F:21])([F:20])[F:19])[O:11][C:10]2[CH:12]=[CH:13][C:14](C=O)=[CH:15][C:9]=2[O:8]1)[C:3]([F:6])([F:5])[F:4].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[Cl:1][CH:2]([C:7]1([C:18]([F:21])([F:19])[F:20])[O:11][C:10]2[CH:12]=[CH:13][C:14]([OH:30])=[CH:15][C:9]=2[O:8]1)[C:3]([F:4])([F:5])[F:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18995949HCID 18995949, compound

Product 1

HCID 189959382-(1-Chloro-2,2,2-trifluoroethyl)-2-(trifluoromethyl)-5-hydroxy-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 g of 2(1-chloro-2,2,2-trifluoroethyl)-2-(trifluoromethyl)-5-formyl-1,3-benzodioxole were dissolved in 500 ml of methylene chloride, and 53 g of 70% by weight m-chloroperbenzoic acid were added. The reaction mixture was stirred under reflux for 6 hours. It was then cooled and the precipitate formed was filtered off. The filtrate was washed with 5% by weight aqueous sodium hydrogen-sulphite solution and saturated aqueous sodium hydrogen-carbonate solution and concentrated on a rotary evaporator. The remaining residue was dissolved in 300 ml of diethyl ether, and 100 ml of 1 N sodium hydroxide solution were added at room temperature. When the reaction was complete, the phases were separated and the organic phase was washed with saturated aqueous ammonium chloride solution, dried over magnesium sulphate and subjected to fractional distillation under vacuum. The yield was 26 g (=54% of theory) and the boiling point was 95° C. at 0.07 mbar. 19F NMR: -68.6 and -81.6 ppm. 1H NMR: 4.70 ppm.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureIt was then cooled
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. washThe filtrate was washed with 5% by weight aqueous sodium hydrogen-sulphite solution and saturated aqueous sodium hydrogen-carbonate solution
  6. concentrationconcentrated on a rotary evaporator
  7. dissolutionThe remaining residue was dissolved in 300 ml of diethyl ether
  8. addition100 ml of 1 N sodium hydroxide solution were added at room temperature
  9. customthe phases were separated
  10. washthe organic phase was washed with saturated aqueous ammonium chloride solution
  11. dry with materialdried over magnesium sulphate
  12. distillationsubjected to fractional distillation under vacuum

Sources & evidence

ORD record
ord-b99914fe8ca64664a127549fdc50c61c
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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