2-Nitrophenol → 1-(2-Methoxyethoxy)-2-nitrobenzene

HRID 322608Notes

Reaction equation

HRID 322608 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH3:11][O:12][CH2:13][CH2:14]Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:11][O:12][CH2:13][CH2:14][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl ether

Product 1

HCID 30173611-(2-Methoxyethoxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

140 g (1010 mmol) 2-nitrophenol, 105 g (1110 mmol) chloroethyl methyl ether, 84.2 g (507 mmol) KI and 153 g (1110 mmol) K2CO3, were suspended in 500 ml DMF, in a 2 l Erlenmeyer flask heated at 110±5° C. for 6 h. The solvent was evaporated and the residue was dissolved in 500 ml CHCl3 and 500 ml water. The organic phase was washed with 2×500 ml 2.5% Na2CO3, 500 ml sat. NaCl and dried over Na2SO4. The solvent was evaporated to afford 201 g (100%) light yellow oil. H1NMR (CDCl3) δ (ppm) 3.45 (s,3H), 3.78(t,2H), 4.25(t,2H), 7.02(dd,1H), 7.10(dd,1H), 7.50(dd,1H), 7.82(dd,1H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 500 ml CHCl3
  3. washThe organic phase was washed with 2×500 ml 2.5% Na2CO3, 500 ml sat. NaCl
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customto afford 201 g (100%) light yellow oil

Sources & evidence

ORD record
ord-51b66877b559444e86e6afc2cb4498be
Source dataset
uspto-grants-2001_04
Patent number
US06211359B1

Reaction notes

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