Réaction #2045020

ord-979c1d994dc040a9be53471a14f4c4a7

Équation de réaction

O=[N+]([O-])c1ccc(O)cc1
4-Nitro phenol
O=C([O-])[O-].[K+].[K+]
K2CO3
COC(=O)CCl
methyl chloroacetate
COC(=O)COc1ccc([N+](=O)[O-])cc1
31
Rendement 72.5%
COC(=O)COc1ccc([N+](=O)[O-])cc1
Methyl(4-Nitro phenoxy)acetate
Rendement 72.5%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurerefluxed for 12 hours
  2. 2
    workup.DISTILLATIONAcetone was distilled off
  3. 3
    workup.ADDITIONwater (1500 ml) added
  4. 4
    FiltrationCrude 31 was filtered
  5. 5
    Autredried
  6. 6
    Autrerecrystallised from a mixture of ethyl acetate:hexane (1:5)

Mode opératoire

To a mixture of 4-Nitro phenol (100 g, 719 mmol) and anhydrous K2CO3 (400 g, 2.894 moles) 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) added. Crude 31 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 31 (110 g, 72.5%) as a white fluffy powder. M.p: 97-98.4° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08409559B2uspto-grants-2013_04