Water → 3-Nitrophenoxyacetic acid methyl ester

HRID 2189018Notes

Reaction equation

HRID 2189018 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:17][O:18][C:19](=[O:22])[CH2:20]Br.O>CC(C)=O>[CH3:17][O:18][C:19](=[O:22])[CH2:20][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 111373-NitrophenolHCID 60984Methyl bromoacetate

Product 1

HCID 107037043-Nitrophenoxyacetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Initially charge 50 g (359.4 mmol) of 3-nitrophenol and 175.67 g (539 mmol) of caesium carbonate in 1.0 liter of acetone and add 71.5 g (467.3 mmol) of bromoacetic acid methyl ester. Stir the mixture at 50° C. for 1 h and, after cooling, pour onto 7.5 liters of water. Stir the suspension for 30 min, then filter off with suction and wash the filter residue with water. Dry the solid in a drying cabinet at 50° C. and 100 mbar. 64.3 g (84.7% of theory) of the target compound are obtained.

Workup

  1. temperatureafter cooling
  2. stirringStir the suspension for 30 min
  3. filtrationfilter off with suction
  4. washwash the filter residue with water
  5. customDry the solid in a drying cabinet at 50° C.
  6. custom64.3 g (84.7% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-1e997f6adffc49e5ac677df267fe6693
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

Loading…