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

HRID 374853Notes

Reaction equation

HRID 374853 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 500 ml of methylene chloride, and 53 g of 70% strength by weight m-chloroperbenzoic acid were added. The mixture was stirred under reflux for 6 hours. It was then cooled, and the precipitate which had separated out was filtered off. The filtrate was washed with 5% strength by weight aqueous sodium hydrogen sulphide solution and with saturated aqueous sodiumbicarbonate solution and concentrated on a rotary evaporator. The residue which remained was dissolved in 300 ml of diethyl ether, and 100 ml of 1N sodium hydroxide solution were added at room temperature. When the reaction had ended, the phases were separated and the organic phase was washed with saturated aqueous ammonium chloride solution, dried with magnesium sulphate and subjected to fractional distillation in vacuo. The yield was 26 g (=54% of theory), and the boiling point was 95° C. under 0.07 mbar. 19F-NMR: -68.6 and -81.6 ppm. 1H-NMR: 4.70 ppm.

Workup

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

Sources & evidence

ORD record
ord-71cbe45d8bbc4418a666aed744259970
Source dataset
uspto-grants-1996_01
Patent number
US05482956

Reaction notes

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