Methyl iodide → 2-Nitro-4-phenylmethoxyanisole

HRID 1090688Notes

Reaction equation

HRID 1090688 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[OH:18])([O-:3])=[O:2].[C:19](=O)([O-])[O-].[K+].[K+].CI>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:18][CH3:19])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 46066344-(Benzyloxy)-2-nitrophenol

Product 1

HCID 156769762-Nitro-4-phenylmethoxyanisole

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

2-Nitro-4-phenylmethoxy-phenol is methylated by contacting it with a slight molar excess of potassium carbonate and a large molar excess of methyl iodide and tetrabutylammonium bromide (TBAB) in an inert solvent (such as acetone) and refluxed for 8 to 15 hours, preferably 12 hours. After cooling, filtration and evaporation of the solvent, the residue is purified by conventional means to give 2-nitro-4-phenylmethoxyanisole, which in turn is hydrogenated to give the corresponding aniline of Formula 12.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration and evaporation of the solvent
  3. customthe residue is purified by conventional means

Sources & evidence

ORD record
ord-6bb8a2e7afc94a3ca05ade756e581829
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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