4-Nitrophenol → 1-[(2-Ethylhexyl)oxy]-4-nitrobenzene

HRID 2245201Notes

Reaction equation

HRID 2245201 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([CH:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:20]I)[CH3:18]>CN1CCCC1=O>[CH2:17]([CH:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:20][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:18]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 102664Heptane, 3-(iodomethyl)-

Product 1

HCID 185198951-[(2-Ethylhexyl)oxy]-4-nitrobenzeneYield 43%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a flask equipped with a magnetic stirrer, reflux condenser, and a nitrogen inlet was added 4-nitrophenol (27.14 grams, 0.195 moles), potassium carbonate (51.13 grams, 0.370 moles), 2-ethylhexyl iodide (45.63, 0.185 moles) in 1-methyl-pyrrolidin-2-one(180 ml). The contents of the flask were heated at 100° C. for 3 hours; cooled to room temperature; partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (3×100 ml). The ethyl acetate extract was washed with a 1 N sodium hydroxide solution (4×75 ml), brine (3×100 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 29.9 grams of crude product as a yellow oil. Excess 2-ethylhexyl iodide was removed from the product using Kugelrohr distillation apparatus to afford 20 grams of pure product as a yellow oil. 1H NMR (CDCl3) δ 8.2(d, 2H), 6.95(d, 2H), 3.95(d, 2H), 1.75(heptet, 1H), 1.2-1.6(m, 8H), 0.85-1.0(m, 6H).

Workup

  1. customTo a flask equipped with a magnetic stirrer
  2. temperaturereflux condenser, and a nitrogen inlet
  3. temperaturecooled to room temperature
  4. custompartitioned between ethyl acetate and water
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×100 ml)
  6. extractionThe ethyl acetate extract
  7. washwas washed with a 1 N sodium hydroxide solution (4×75 ml), brine (3×100 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto yield 29.9 grams of crude product as a yellow oil
  12. customExcess 2-ethylhexyl iodide was removed from the product
  13. distillationKugelrohr distillation apparatus

Sources & evidence

ORD record
ord-6693a0a1d79149dfb9fc626d53b07edf
Source dataset
uspto-grants-2010_03
Patent number
US07683017B2

Reaction notes

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