Water → HCID 18520594, compound

HRID 1368773Notes

Reaction equation

HRID 1368773 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.[OH-].[Na+].O>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][CH2:13][CH:15]1[O:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 2230832,4-Difluoro-6-nitrophenol

Product 1

HCID 18520594HCID 18520594, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture consisting of 12.62 g of 2,4-difluoro-6-nitrophenol, 36 ml of epichlorohydrin, 3.3 g of sodium hydroxide, 15 ml of water and 320 ml of ethanol was stirred at 80° C. for 24 hours. After cooling the reaction solution to room temperature, the insoluble matter was removed by filtration and the filtrate was concentrated to dryness under a reduced pressure. The resulting residue was dissolved in an ether-hexane (1:2) mixed solvent, washed with water and saturated brine and dried with anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The residue was applied to a silica gel column chromatography and developed with an ethyl acetate-hexane (1:9) mixed solvent, and then the fractions containing the compound of interest were concentrated to obtain 11.28 g of the title compound.

Workup

  1. temperatureAfter cooling the reaction solution to room temperature
  2. customthe insoluble matter was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness under a reduced pressure
  4. dissolutionThe resulting residue was dissolved in an ether-hexane (1:2)
  5. additionmixed solvent
  6. washwashed with water and saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. additionmixed solvent
  10. additionthe fractions containing the compound of interest
  11. concentrationwere concentrated

Sources & evidence

ORD record
ord-466d72e675f14be484a4116b56d017e2
Source dataset
uspto-grants-2003_06
Patent number
US06573377B1

Reaction notes

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