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

HRID 1957840Notes

Reaction equation

HRID 1957840 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-1dd43a54551a4a04beecc93061afbc03
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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