Sulfuric Acid → 3-Hydroxy-4-nitrobenzonitrile

HRID 1419412Notes

Reaction equation

HRID 1419412 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-1d0638c6ac1b413ab17c2e143b385741
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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