4-Nitrophenol → 2-((4-Nitrophenoxy)methyl)oxirane

HRID 1904393Notes

Reaction equation

HRID 1904393 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl>[OH-].[Na+]>[O:15]1[CH:13]([CH2:11][O:10][C:3]2[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 7835Epichlorohydrin

Product 1

HCID 213272-((4-Nitrophenoxy)methyl)oxirane

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

p-Nitrophenol (139 g, 1.0 mol) was dissolved in 1.5 l 0.8M sodium hydroxide. Epichlorohydrin, IX, (117 ml, 1.5 mol) was added and the mixture stirred vigorously overnight. The homogenous solution was then extracted three times with 300 ml chloroform and the organic fractions combined and dried over magnesium sulfate. After removal of the drying agent by filtration, evaporation of the filtrate gave a yellow oil which crystallized on standing. The oily crystals were triturated with methanol and filtered to yield 55.6 g of the desired compound as white crystals shown to be homogenous by thin layer chromatography (60:40 ethyl acetate/hexanes, Rf =0.77) m.p. 62°-65° C.

Workup

  1. extractionThe homogenous solution was then extracted three times with 300 ml chloroform
  2. dry with materialdried over magnesium sulfate
  3. customAfter removal of the drying agent
  4. filtrationby filtration, evaporation of the filtrate
  5. customgave a yellow oil which
  6. customcrystallized
  7. customThe oily crystals were triturated with methanol
  8. filtrationfiltered

Sources & evidence

ORD record
ord-b7867968a9fa4f0587d9a1f6b698ca9d
Source dataset
uspto-grants-1989_06
Patent number
US04837305

Reaction notes

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