Nitric Acid → 4-Hydroxy-3-nitrobenzonitrile

HRID 1944694Notes

Reaction equation

HRID 1944694 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1>C(O)(=O)C>[OH:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 130194-Cyanophenol

Product 1

HCID 767584-Hydroxy-3-nitrobenzonitrileYield 79.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of nitric acid (1.16 g, 12 mmol) and glacial acetic acid (1 mL) was heated to 40° C. To this mixture was added rapidly a solution of 4-hydroxybenzonitrile (1 g, 8.4 mmol) in glacial acetic acid (4 mL) until the flask temperature rose to 50° C. Then the solution was added at a rate such that the temperature was maintained at 50-60° C. When addition was complete the mixture was stirred for another 20 min at 55° C., and then poured into ice-water (24 mL). The mixture was filtered and the solid was washed with water to give 4-hydroxy-3-nitrobenzonitrile 1.09 g (79%) as a solid.

Workup

  1. customrose to 50° C
  2. additionThen the solution was added at a rate such that the temperature
  3. temperaturewas maintained at 50-60° C
  4. additionWhen addition
  5. filtrationThe mixture was filtered
  6. washthe solid was washed with water

Sources & evidence

ORD record
ord-4c8e882e070d432c9c3066767c8bb99a
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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