Water → HCID 21436781, compound

HRID 2397882Notes

Reaction equation

HRID 2397882 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[N+:18]([O-:23])([N+]([O-])=O)=[O:19].O>C(O)(=O)C.C(OCC)C.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([N+:18]([O-:23])=[O:19])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25352Nitrogen oxide (N2O4)HCID 21436798HCID 21436798, compound

Product 1

HCID 21436781HCID 21436781, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 5.3 g (0.024 mole) of 7 -methoxy-3-phenylbenzofuran in 200 ml of acetic acid is added dropwise 3.3 g (0.036 mole) of dinitrogen tetroxide in 20 ml of acetic acid. After about 90 minutes the mixture is poured into cold water, precipitating a gum which is isolated by filtration and dissolved in diethyl ether. The ether solution is washed with water and saturated sodium chloride solution and dried. Evaporation gives a residue which is dissolved in chloroform and eluted through a silica gel column with chloroform. Early fractions are a yellow solid which is recrystallized from ethanol to give yellow crystals of 7-methoxy-2-nitro-3-phenylbenzofuran, m.p. 160°-161° C.

Workup

  1. customprecipitating a gum which
  2. customis isolated by filtration
  3. washThe ether solution is washed with water and saturated sodium chloride solution
  4. customdried
  5. customEvaporation
  6. customgives a residue which
  7. washeluted through a silica gel column with chloroform
  8. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-14c04635fd974bbe89584ec8b8ccfc05
Source dataset
uspto-grants-1977_05
Patent number
US04022908

Reaction notes

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