Potassium Hydroxide → 2-(2,4-Difluorophenyl)-1,2,3-propanetriol

HRID 2256470Notes

Reaction equation

HRID 2256470 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:20])([CH2:15][O:16]C(=O)C)[CH2:10][O:11]C(=O)C.[OH-].[K+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:20])([CH2:15][OH:16])[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 154634621,3-Diacetoxy-2-(2,4-difluorophenyl)-2-propanol

Product 1

HCID 112179522-(2,4-Difluorophenyl)-1,2,3-propanetriolYield 91.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 200 ml reaction vessel, 10 g of 2-(2,4-difluorophenyl)-1,3-diacetoxy-2-propanol was dissolved in 30 ml of toluene and thereto was added 30 ml of 30% aqueous KOH solution. The resulting liquid was stirred at room temperature for 24 hours and more. Then a toluene-layer and an aqueous layer were separated from each other and the aqueous layer was extracted twice with 50 ml of ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was removed therefrom and the residue was purified in the same manner as in Example 32 to give 6.5 g of 2-(2,4-difluorophenyl)-1,2,3-propanetriol.

Workup

  1. customThen a toluene-layer and an aqueous layer were separated from each other and the aqueous layer
  2. extractionwas extracted twice with 50 ml of ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified in the same manner as in Example 32

Sources & evidence

ORD record
ord-2c4f0423486043c4baf8ccea4391389d
Source dataset
uspto-grants-1997_08
Patent number
US05654472

Reaction notes

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