Nitric Acid → 2-Hydroxy-5-nitrobenzonitrile

HRID 1656651Notes

Reaction equation

HRID 1656651 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[OH:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].O>C(OCC)(=O)C>[OH:10][C:11]1[CH:18]=[CH:17][C:16]([N+:1]([O-:4])=[O:2])=[CH:15][C:12]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 119072-Hydroxybenzonitrile

Product 1

HCID 111163772-Hydroxy-5-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 70 ml. 40% nitric acid and 10 ml. concentrated sulphuric acid is added dropwise at 10° C. in the course of 1 hour to 24 g. (0.2 mole) 2-hydroxybenzonitrile in 20 ml. water. The reaction mixture is subsequently stirred for 24 hours at 20° C. and then shaken out with 100 ml. ethyl acetate. After evaporation of the organic solvent, the solid residue obtained is extracted twice with 500 ml. amounts of boiling n-hexane. Purification takes place by means of column chromatography on silica gel (silica gel 60; elution agent ethyl acetate). After evaporation of the solvent and crystallisation from ethyl acetate/toluene, there are obtained 2 g. of the desired product in the form of white crystals.

Workup

  1. stirringshaken out with 100 ml
  2. customAfter evaporation of the organic solvent
  3. customthe solid residue obtained
  4. extractionis extracted twice with 500 ml
  5. customPurification
  6. customAfter evaporation of the solvent and crystallisation from ethyl acetate/toluene, there
  7. customare obtained 2 g

Sources & evidence

ORD record
ord-75ef777852aa4439a69df00814d1d5d2
Source dataset
uspto-grants-1993_10
Patent number
US05254677

Reaction notes

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