Sulfuric Acid → 2-Hydroxy-3-nitrobiphenyl

HRID 568064

Reaction equation

HRID 568064 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:14]([O-])([O-:16])=[O:15].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]=1[OH:13])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7017(1,1'-Biphenyl)-2-olHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

Product 1

HCID 1607452-Hydroxy-3-nitrobiphenylYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-phenylphenol (3.00 g, 17.6 mmol) was dissolved in methylene chloride(40 ml) followed by the addition of sodium nitrate (1.65 g, 19.4 mmol). The addition of sulfuric acid (25 ml/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hrs, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(900 mg, 24%). 1H NMR (CD3COCD3): δ 8.19 (d,1H), 7.79 (d,1H), 7.64 (d, 2H), 7.50 (t, 2H), 7.45 (t, 1H), 7.22 (t, 1H).

Workup

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b522c8bf3123459cad5288be78864b65
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Linked notes

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