Réaction #2045018

ord-4d0e68b9a7924dffa769b09b79c684ed

Équation de réaction

COC(=O)COc1ccc(N=C=O)cc1
(4-Isocyanato-phenoxy)-acetic acid methyl ester
OCCO
ethylene glycol
COC(=O)COc1ccc(NC(=O)OCCO)cc1
29
Rendement 82.9%
COC(=O)COc1ccc(NC(=O)OCCO)cc1
[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-acetic acid methyl ester
Rendement 82.9%

Solvants

Conditions de réaction

Température
42°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Filtrationcrude 29 was filtered
  2. 2
    Autredried
  3. 3
    Autrepurified by column chromatography on silica gel

Mode opératoire

(4-Isocyanato-phenoxy)-acetic acid methyl ester 28 (15 g, 72.46 mmol) was added to ethylene glycol (30 ml) at room temperature. The reaction was exothermic and the temperature raised to 42° C. Later the reaction mixture was stirred at room temperature for 16 hours. Water (100 ml) was added and crude 29 was filtered, dried and purified by column chromatography on silica gel using chloroform as eluant to get pure 29 (16.17 g, 82.9%) as a off-white powder. M.p: 85.5-87.5° C.

Source

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