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

HRID 2169718Notes

Reaction equation

HRID 2169718 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-Isocyanato-phenoxy)-propionic acid methyl ester 32 (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. The mixture was allowed to cool and later stirred at room temperature for 16 hours. Water (150 ml) was added and crude 33 was extracted into chloroform, washed with water (2×50 ml), dried over sodium sulphate and distilled. Crude 33 was purified by column chromatography on silica gel using chloroform as eluant to get pure 33 (13 gr, 50.76%) as a syrup which crystallized in 48 hours as a white powder. M.p: 90.5-92.8° C.

Workup

  1. customrose to 58° C
  2. temperatureto cool
  3. extractioncrude 33 was extracted into chloroform
  4. washwashed with water (2×50 ml)
  5. dry with materialdried over sodium sulphate
  6. distillationdistilled
  7. customCrude 33 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-43e54a2a9640491d9cb6eedaccb1fd3d
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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