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

HRID 564878Notes

Reaction equation

HRID 564878 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. The reaction mixture was cooled to room temperature, and any insoluble matter was removed by filtration. The filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in a 1:1 mixed solvent of diethyl ether and hexane, washed with water and then with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography using a 3:1 mixture of chloroform and hexane as a developing solvent. The fraction containing the desired compound was concentrated to give 27.9 g of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customany insoluble matter was removed by filtration
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in a 1:1 mixed solvent of diethyl ether and hexane
  5. washwashed with water
  6. dry with materialwith a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. additiona 3:1 mixture of chloroform and hexane as a developing solvent
  9. additionThe fraction containing the desired compound
  10. concentrationwas concentrated

Sources & evidence

ORD record
ord-84ff919e53fe4ce19c92a2313c69d4d6
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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