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

HRID 618224Notes

Reaction equation

HRID 618224 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-17a2368ef58c408d9b99370d47afeb2f
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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