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

HRID 83801Notes

Reaction equation

HRID 83801 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-4c3739d0256e4b70b975b6c59eac8186
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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