1-(3-Methoxyphenoxy)-2-nitrobenzene → 3-(2-Nitrophenoxy)phenol

HRID 1609259Notes

Reaction equation

HRID 1609259 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([O:13]C)[CH:10]=[CH:11][CH:12]=1)([O-:3])=[O:2].Cl.N1C=CC=CC=1>O>[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 93111371-(3-Methoxyphenoxy)-2-nitrobenzeneHCID 10176127Pyridinium chloride

Product 1

HCID 125886933-(2-Nitrophenoxy)phenolYield 87.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 28.8 g of 3-(2-nitrophenoxy)anisole and 68 g of pyridine hydrochloride was heated to 160°-170° C. to prepare a homogeneous solution, which was further heated at 195°-205° C. with stirring for one hour. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried and concentrated and the residue was subjected to silica gel and eluted with chloroform to give 23.8 g of the title compound as a light brown oil.

Workup

  1. temperaturewas heated to 160°-170° C.
  2. customto prepare a homogeneous solution, which
  3. temperaturewas further heated at 195°-205° C.
  4. temperatureAfter cooling
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. customdried
  8. concentrationconcentrated
  9. washeluted with chloroform

Sources & evidence

ORD record
ord-88446460ee1a4c2996d1b240bab33973
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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