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

HRID 1003766Notes

Reaction equation

HRID 1003766 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 as 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 as 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-a82a8e980fdd47fc87c02f1d9bd06056
Source dataset
uspto-grants-2000_04
Patent number
US06046354

Reaction notes

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