Guaiacol → HCID 22663746, compound

HRID 392386Notes

Reaction equation

HRID 392386 reaction equation
F[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.ClCCl>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 460GuaiacolHCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 22663746HCID 22663746, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 3-fluoronitrobenzene (3.53 g, 25 mmol) and 2-methoxyphenol (3.72 g, 30 mmol) in anhydrous N,N-dimethylformamide (25 mL) under nitrogen was treated with anhydrous potassium carbonate (7.6 g, 55 mmol) and heated to 110° C. for 65 h, then cooled to room temperature. The solution was diluted with dichloromethane (50 ml) and treated with DOWEX® 550A OH anion exchange resin (log) which had been washed dry with methanol. Stirring was continued for one hour, the mixture was filtered, and the filtrate concentrated in vacuo (exhaustively at end to remove DMF) to give 3-(2-methoxyphenoxy)nitrobenzene as a residue.

Workup

  1. temperaturecooled to room temperature
  2. washhad been washed
  3. dry with materialdry with methanol
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate concentrated in vacuo (exhaustively at end
  6. customto remove DMF)

Sources & evidence

ORD record
ord-cf6eed5a91fe4c899acababbddb64ead
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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