Nitric Acid → 2-Hydroxy-3-methyl-5-nitro-benzonitrile

HRID 636710Notes

Reaction equation

HRID 636710 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[OH:10])#[N:2].[N+:11]([O-])([OH:13])=[O:12].O>C(O)(=O)C>[C:1]([C:3]1[CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=[C:5]([CH3:9])[C:4]=1[OH:10])#[N:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 143886552-Hydroxy-3-methylbenzonitrile

Product 1

HCID 212556572-Hydroxy-3-methyl-5-nitro-benzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
45 °C

Procedure

To a heated (45° C.), stirred solution of 2-cyano-6-methylphenol (5 g) in glacial acetic acid (32 mL) was added a solution of fuming nitric acid (3.2 mL) in acetic acid (12 mL). After 1 h at elevated temperature (45° C.), the reaction mixture was cooled (to 0° C.), water added and partitioned between DEE/water. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo to afford a solid. Recrystallization from DEE afforded the title compound as yellow crystals (3.6 g).

Workup

  1. additionadded
  2. custompartitioned between DEE/water
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a solid
  7. customRecrystallization from DEE

Sources & evidence

ORD record
ord-418ea8f2777c4d5c9453a9cc0359d90b
Source dataset
uspto-grants-2001_02
Patent number
US06194454B1

Reaction notes

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