Water → 1-(4-Fluoro-2-nitrophenoxy)-2,3-epoxypropane

HRID 1368769Notes

Reaction equation

HRID 1368769 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl.[OH-].[Na+].O>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH:14]2[O:16][CH2:15]2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 1362364-Fluoro-2-nitrophenol

Product 1

HCID 185204241-(4-Fluoro-2-nitrophenoxy)-2,3-epoxypropane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture consisting of 31.4 g of 4-fluoro-2-nitrophenol, 100 ml of epichlorohydrin, 9.1 g of sodium hydroxide, 40 ml of water and 900 ml of ethanol was stirred at 80° C. for 10 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 (1:1) 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 a chloroform-hexane (3:1) mixed solvent, and then the fractions containing the compound of interest were concentrated to obtain 27.9 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 (1:1)
  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-6e89a7b4fecd41de850251bace2a3e9f
Source dataset
uspto-grants-2003_06
Patent number
US06573377B1

Reaction notes

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