Acetic Acid → 1,3-Diacetoxy-2-(2,4-difluorophenyl)-2-propanol

HRID 356807Notes

Reaction equation

HRID 356807 reaction equation
Cl[CH2:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[F:13])[O:5][CH2:4]1.[C:14]([OH:17])(=[O:16])[CH3:15].[C:18]([O-:21])(=[O:20])[CH3:19].[K+]>O>[C:14]([O:17][CH2:2][C:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])([OH:5])[CH2:4][O:21][C:18](=[O:20])[CH3:19])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517044Potassium AcetateHCID 111833262-(Chloromethyl)-2-(2,4-difluorophenyl)oxirane

Product 1

HCID 154634621,3-Diacetoxy-2-(2,4-difluorophenyl)-2-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

To 105 g of 1-chloro-2-(2,4-difluorophenyl)-2,3-epoxypropane were added 525 ml of acetic acid and 126 g of potassium acetate and the resulting mixture was stirred at 115° C. for 15 hours. The reaction mixture was allowed to cool to room temperature. Then, to this reaction liquid was added 700 ml of water and a solid matter was dissolved and the resulting solution was extracted three times with 500 ml of ethyl acetate. The organic layer was washed with saturated aqueous solution with sodium hydrogencarbonate and with water and dried over anhydrous sodium sulfate. The resulting organic layer was filtered and the solvent was removed under reduced pressure. Thus obtained concentrate was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 100 g of the desired compound.

Workup

  1. temperatureto cool to room temperature
  2. customThen, to this reaction liquid
  3. dissolutiona solid matter was dissolved
  4. extractionthe resulting solution was extracted three times with 500 ml of ethyl acetate
  5. washThe organic layer was washed with saturated aqueous solution with sodium hydrogencarbonate and with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe resulting organic layer was filtered
  8. customthe solvent was removed under reduced pressure
  9. customThus obtained
  10. concentrationconcentrate
  11. customwas purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8745f8f788a143389e207bff7da30607
Source dataset
uspto-grants-1998_11
Patent number
US05840553

Reaction notes

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