Reacción #170960

ord-babbe404bc1e4121af8d645fddc011eb

Ecuación de reacción

O=[N+]([O-])c1ccc(O)cc1
4-nitrophenol
O=C([O-])[O-].[K+].[K+]
K2CO3
COC(=O)CCl
methyl chloroacetate
COC(=O)COc1ccc([N+](=O)[O-])cc1
7
Rendimiento 72.5%
COC(=O)COc1ccc([N+](=O)[O-])cc1
Methyl (4-Nitro phenoxy)acetate
Rendimiento 72.5%

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturarefluxed for 12 hours
  2. 2
    workup.DISTILLATIONAcetone was distilled off
  3. 3
    workup.ADDITIONwater (1500 ml) was added
  4. 4
    FiltraciónCrude 7 was filtered
  5. 5
    Otrodried
  6. 6
    Otrorecrystallised from a mixture of ethyl acetate:hexane (1:5)

Procedimiento

To a mixture of 4-nitrophenol (100 g, 719 mmol) and anhydrous K2CO3 (400 gm, 2.894 mol) in anhydrous acetone (950 ml) was added methyl chloroacetate (114 g, 1.050 moles) and refluxed for 12 hours. Acetone was distilled off and water (1500 ml) was added. Crude 7 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 7 (110 g, 72.5%) as a white fluffy powder with an m.p between 97-98.4° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08846845B2uspto-grants-2014_09