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

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Reaction Conditions

Reaction Steps

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).

Provenance & Evidence