Sulfuric Acid → 3-Hydroxy-4-nitrobenzonitrile

HRID 568036Notes

Reaction equation

HRID 568036 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].[N+:10]([O-])([O-:12])=[O:11].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:10]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[OH:9])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 133943-CyanophenolHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

Product 1

HCID 151119213-Hydroxy-4-nitrobenzonitrileYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-cyanophenol (2.38 g, 20 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.88 g, 22 mmol). The addition of sulfuric acid (20 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, 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(910 mg, 28%). 1H NMR (CD3COCD3): δ 8.30 (d,1H), 7.67 (s,1H), 7.49 (d, 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-32a8b43c2f524faab69eb8c8fa4c7d14
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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