Ethylene Glycol → 2-[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-propionic acid methyl ester

HRID 83784Notes

Reaction equation

HRID 83784 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:14]=[O:15])=[CH:9][CH:8]=1)[CH3:5].[CH2:17]([OH:20])[CH2:18][OH:19]>O>[CH3:1][O:2][C:3](=[O:16])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:19][CH2:18][CH2:17][OH:20])=[O:15])=[CH:9][CH:8]=1)[CH3:5]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 497643632-(4-Isocyanato-phenoxy)-propionic acid methyl ester

Product 1

HCID 592539572-[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-propionic acid methyl esterYield 50.76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-Isocyanatophenoxy)-propionic acid methyl ester 11 (20 g, 90.49 mmol) was added to ethylene glycol (40 ml) at room temperature. The reaction was exothermic and the temperature rose to 58° C. This was followed by stifling at room temperature for 16 hours. Water (150 ml) was added and crude 12 was extracted in to chloroform, washed with water (2×50 ml), dried over sodium sulphate and distilled. Crude 12 was purified by column chromatography on silica gel using chloroform as eluant to get pure 12 (13 g, 50.76%) as a syrup which crystallized in 48 hours as a white powder with an m.p between 90.5-92.8° C.

Workup

  1. customrose to 58° C
  2. extractioncrude 12 was extracted in to chloroform
  3. washwashed with water (2×50 ml)
  4. dry with materialdried over sodium sulphate
  5. distillationdistilled
  6. customCrude 12 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e512b71118274119882b20be98f8211b
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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