4-Nitrophenol → Sodium 2-nitrophenolate

HRID 1382473Notes

Reaction equation

HRID 1382473 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+:12].[O:13]1CCCC1>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O-:13])([O-:3])=[O:2].[Na+:12]

Participants

4

Reactant 3

HCID 9804-NitrophenolHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydride

Product 1

HCID 69985Sodium 2-nitrophenolateYield 30%

Procedure

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.

Workup

  1. additionThis solution is slowly added to the flask
  2. temperatureThe resulting solution is refluxed for sixty-five hours
  3. temperatureAfter this time the reaction mixture is cooled
  4. filtrationfiltered
  5. customto remove sodium chloride
  6. washwashed with hot tetrahydrofuran
  7. concentrationThe filtrate is concentrated
  8. additionpoured
  9. customover crushed ice
  10. washThe gummy oil is washed with large quantities of water and methanol
  11. customdried in a dessicator

Sources & evidence

ORD record
ord-0e25479d914d47ecbc3e372e54035545
Source dataset
uspto-grants-1989_02
Patent number
US04806607

Reaction notes

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