Nitric Acid → (4-Hydroxy-3-nitro-phenoxy)-acetonitrile

HRID 1106731Notes

Reaction equation

HRID 1106731 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13].C(OCC)(=O)C>[N+](C)([O-])=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 137506092-(4-Hydroxyphenoxy)acetonitrile

Product 1

HCID 18789604(4-Hydroxy-3-nitro-phenoxy)-acetonitrile

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A solution of 7.5 g of (4-hydroxy-phenoxy)-acetonitrile dissolved in 60 ml of nitromethane was cooled in an ice bath and 3.88 ml of 70% nitric acid was added dropwise. After 45 minutes, the reaction mixture was poured into ethyl acetate, washed with brine, dried (MgSO4), and evaporated to dryness. The crude product was purified by silica gel chromatography eluting with ethyl acetate/hexane (1:3), giving 5.45 g of (4-hydroxy-3-nitro-phenoxy)-acetonitrile as a yellow solid, mp 113.1-114.1° C.

Workup

  1. temperaturewas cooled in an ice bath
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-48ac53ddc23e452e8daf701e553c2682
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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