Nitric Acid → 2-Nitro-4-phenoxyphenol

HRID 2075259Notes

Reaction equation

HRID 2075259 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:15]([O-])([OH:17])=[O:16]>CC(O)=O>[N+:15]([C:10]1[CH:9]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][C:11]=1[OH:14])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 132544-Phenoxyphenol

Product 1

HCID 107758492-Nitro-4-phenoxyphenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-phenoxyphenol (10.0 g, 54 mmol) in 100 mL AcOH was added slowly dropwise nitric acid (69-70%, 3.2 mL, 54 mmol) over about 3 min from an addition funnel. The reaction became warm and was cooled with a water bath. After 1 h, the reaction was poured onto ice and allowed to warm to rt. A gummy solid resulted, which was partitioned between MTBE and water. The organic layer was washed 1× water, 1× brine, dried over sodium sulfate, filtered, and concentrated to a dark oil. This was adsorbed onto 36 g silica gel and dried, and purified in two parts by silica gel chromatography, ISCO, 0-10% EtOAC/hexanes. Product-containing fractions were combined and concentrated to give 2-nitro-4-phenoxyphenol as an orange oil. MS (ESI) m/z: Calculated: 231.1; Observed: 230.0 (M−−1).

Workup

  1. temperatureThe reaction became warm
  2. temperaturewas cooled with a water bath
  3. additionthe reaction was poured onto ice
  4. customA gummy solid resulted
  5. customwhich was partitioned between MTBE and water
  6. washThe organic layer was washed 1× water, 1× brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to a dark oil
  10. customdried
  11. custompurified in two parts by silica gel chromatography, ISCO, 0-10% EtOAC/hexanes
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-d06aa4e2f5a94283a2fde90b393400c3
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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