Réaction #2045035

ord-b2d373b25ed84322810d7490682acdcc

Équation de réaction

CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)O
2-(4-Nitro-phenoxy)-propionic acid
OCCO
ethylene glycol
Cl
HCl
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)OCCO
48
Rendement 56.8%
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)OCCO
2-(4-Nitro-phenoxy)-propionic acid 2-hydroxy-ethyl ester
Rendement 56.8%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrefor 1½ hours
  2. 2
    AutreDuring HCl gas bubbling the temp
  3. 3
    Autrerose to 60° C
  4. 4
    AutreThe crude reaction mass
  5. 5
    ExtractionCrude 48 was extracted into chloroform
  6. 6
    Séchagedried over Na2SO4
  7. 7
    workup.DISTILLATIONdistilled
  8. 8
    Autrepurified by column chromatography on silica gel

Mode opératoire

To a mixture of 2-(4-Nitro-phenoxy)-propionic acid 47 (45 g, 213 mol) and ethylene glycol (135 ml) was passed dry HCl gas for 1½ hours. During HCl gas bubbling the temp. rose to 60° C. The crude reaction mass was poured onto cold water (600 ml). Crude 48 was extracted into chloroform, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 48 (28 g, 56.8%) as a syrup.

Source

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