4-Nitrophenol → Sodium 2-nitrophenolate

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Reaction Steps

A solution of sodium nitrophenoxide is prepared by slowly adding a solution of 4-nitrophenol (119.6 g, 0.86 moles) in 285 mls tetrahydrofuran to a cooled slurry of sodium hydride (34.4 g of a 60% mineral oil dispersion, 0.86 moles) in 285 mls tetrahydrofuran. This solution is slowly added to the flask containing the phosphazene mixture. The resulting solution is refluxed for sixty-five hours. After this time the reaction mixture is cooled, filtered to remove sodium chloride and washed with hot tetrahydrofuran. The filtrate is concentrated, poured over crushed ice and macerated. The gummy oil is washed with large quantities of water and methanol, and dried in a dessicator to yield 71.6 of of a light brown solid (30% yield based on the phosphazene starting material). 31P NMR (DMSO) δ8.8(m), δ-12.8 (m); 1H NMR (DMSO-d6) δ8.1 (d, J=7 Hz), δ7.4-6.7 (unresolved), relative intensities 1:5.

Provenance & Evidence