Anisole → HCID 13425547, compound

HRID 1249324Notes

Reaction equation

HRID 1249324 reaction equation
F[B-](F)(F)F.[N+:6]([C:9]1[CH:10]=[C:11]([N+]#N)[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7].C([O-])(=O)C.[K+].[C:22]1([O:28][CH3:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:29][O:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=1

Participants

4

Reactant 3

HCID 7519AnisoleHCID 517044Potassium AcetateHCID 11665863HCID 11665863, compound

Product 1

HCID 13425547HCID 13425547, compound

Procedure

Anisole (400 mL) and 3-nitrobenzenediazonium tetrafluoroborate (54.5 g, 0.23 mol) were placed in a 1-L flask and stirred mechanically. Potassium acetate (49.0 g, 0.5 mol) was added in one portion. The mixture turned red and warmed slightly. Stirring was continued 12 h., then the solution was filtered and the anisole evaporated in vacuo. Column chromatography of the residue (alumina, 0-10% ether/hexane, first yellow band) and recrystallization (95% EtOH) provided pure 2-methoxy-3'-nitrobiphenyl: 18 g (35%); mp 68°-69° C.

Workup

  1. temperaturewarmed slightly
  2. stirringStirring
  3. filtrationthe solution was filtered
  4. customthe anisole evaporated in vacuo
  5. customColumn chromatography of the residue (alumina, 0-10% ether/hexane, first yellow band) and recrystallization (95% EtOH)

Sources & evidence

ORD record
ord-d18e8faf045b4f39a44730e00eb674e4
Source dataset
uspto-grants-1986_12
Patent number
US04631119

Reaction notes

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