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

HRID 2169731Notes

Reaction equation

HRID 2169731 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-72a2b2a33e9641abbaf71f369cbf801b
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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