Nitric Acid → (1,1'-Biphenyl)-3-ol, 4-nitro-

HRID 568009Notes

Reaction equation

HRID 568009 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[N+:14]([C:10]1[CH:11]=[CH:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][C:9]=1[OH:13])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 113813-Phenylphenol

Product 1

HCID 87437(1,1'-Biphenyl)-3-ol, 4-nitro-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-phenyl phenol(2 g, 11 mmol) in acetic acid was treated with concentrated nitric acid drop-wise until all starting material was consumed. The solution was partitioned between water and methylene chloride. The organic phase was separated and the aqueous phase was extracted once more with methylene chloride. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography(ethyl acetate/hexanes) to afford desired (1.2 g, 50%). 1H NMR (CDCl3): δ 10.65(s, 1H), 8.18 (d, 1H, J=10.0 Hz), 7.65 (d, 2H, J=6.0 Hz), 7.49 (m, 3H), 7.34 (s, 1H), 7.10 (d, 1H, J=10.0 Hz).

Workup

  1. customwas consumed
  2. customThe solution was partitioned between water and methylene chloride
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted once more with methylene chloride
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography(ethyl acetate/hexanes)
  9. customto afford

Sources & evidence

ORD record
ord-27c9a8d7df9f4908a09bfec631fb8e5a
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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