Potassium Hydroxide → 2-(Chloromethyl)-2-(2,4-difluorophenyl)oxirane

HRID 2256462Notes

Reaction equation

HRID 2256462 reaction equation
[Cl:1][CH2:2][C:3]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[F:14])([OH:6])[CH2:4]Cl.[OH-].[K+]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]1([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=2[F:14])[O:6][CH2:4]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 112879311,3-Dichloro-2-(2,4-difluorophenyl)-2-propanol

Product 1

HCID 111833262-(Chloromethyl)-2-(2,4-difluorophenyl)oxiraneYield 50.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 1.7 l of toluene solution of 433 g of 1,3-dichloro-2-(2,4-difluorophenyl)-2-propanol was added 870 ml of 20% aqueous solution of potassium hydroxide. After the resulting liquid was stirred at room temperature for 3 hours, the organic layer was separated therefrom. The aqueous layer was extracted twice with 1 l of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The resulting organic layer was filtered and the solvent was removed under reduced pressure. Thus obtained concentrate was distilled under reduced pressure to give 184 g of the desired compound.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice with 1 l of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe resulting organic layer was filtered
  5. customthe solvent was removed under reduced pressure
  6. customThus obtained
  7. concentrationconcentrate
  8. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-bb988febdeac484da9ebf758d7dab687
Source dataset
uspto-grants-1997_08
Patent number
US05654472

Reaction notes

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