Reacción #725918

ord-78255972c4214702b3f50077c05af978

Ecuación de reacción

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
Rendimiento 56.8%
CC(Oc1ccc([N+](=O)[O-])cc1)C(=O)OCCO
2-(4-Nitro-phenoxy)-propionic acid 2-hydroxy-ethyl ester
Rendimiento 56.8%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrofor 1½ hours
  2. 2
    OtroDuring HCl gas bubbling the temp
  3. 3
    Otrorose to 60° C
  4. 4
    OtroThe crude reaction mass
  5. 5
    ExtracciónCrude 48 was extracted into chloroform
  6. 6
    Secadodried over Na2SO4
  7. 7
    workup.DISTILLATIONdistilled
  8. 8
    Otropurified by column chromatography on silica gel

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07691364B2uspto-grants-2010_04