Ethylene Glycol → 2-(4-Nitrophenoxy)-propionic acid 2-hydroxy-ethyl ester

HRID 1098719Notes

Reaction equation

HRID 1098719 reaction equation
Cl.[N+:2]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:17](O)[CH2:18][OH:19]>O>[OH:19][CH2:18][CH2:17][O:12][C:11](=[O:13])[CH:10]([O:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:16][CH:15]=1)[CH3:14]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 38051392-(4-Nitrophenoxy)propanoic acid

Product 1

HCID 592539752-(4-Nitrophenoxy)-propionic acid 2-hydroxy-ethyl esterYield 56.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dry HCl gas was passed through a mixture of 2-(4-nitrophenoxy)-propionic acid 29 (45 g, 213 mol) and ethylene glycol (135 ml) for 1½ hours. During HCl gas bubbling the temperature rose to 60° C. The crude reaction mass was poured onto cold water (600 ml). Crude 30 was extracted into chloroform, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 30 (28 g, 56.8%) as a syrup.

Workup

  1. customDuring HCl gas bubbling the temperature
  2. customrose to 60° C
  3. customThe crude reaction mass
  4. extractionCrude 30 was extracted into chloroform
  5. dry with materialdried over Na2SO4
  6. distillationdistilled
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d306e8544d6e4223bf322f29958cfc5d
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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