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

HRID 1957853Notes

Reaction equation

HRID 1957853 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:16](O)[CH2:17][OH:18].Cl>O>[OH:18][CH2:17][CH2:16][O:11][C:10](=[O:12])[CH:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)[CH3:13]

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

To a mixture of 2-(4-Nitro-phenoxy)-propionic acid 47 (45 g, 213 mol) and ethylene glycol (135 ml) was passed dry HCl gas for 1½ hours. During HCl gas bubbling the temp. rose to 60° C. The crude reaction mass was poured onto cold water (600 ml). Crude 48 was extracted into chloroform, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 48 (28 g, 56.8%) as a syrup.

Workup

  1. customfor 1½ hours
  2. customDuring HCl gas bubbling the temp
  3. customrose to 60° C
  4. customThe crude reaction mass
  5. extractionCrude 48 was extracted into chloroform
  6. dry with materialdried over Na2SO4
  7. distillationdistilled
  8. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b2d373b25ed84322810d7490682acdcc
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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