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

HRID 612664Notes

Reaction equation

HRID 612664 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 solution 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): δ10.65 (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=10.0Hz).

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 solution 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-b5331ed133bf4badbed5bc189d810fa5
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

Loading…