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

HRID 1957847Notes

Reaction equation

HRID 1957847 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH2:16](O)[CH2:17][OH:18]>>[OH:18][CH2:17][CH2:16][O:11][C:10](=[O:12])[CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 15720(4-Nitrophenoxy)acetic acid

Product 1

HCID 59253945(4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl esterYield 57.4%

Procedure

To a mixture of (4-nitrophenoxy)acetic acid 40 (100 g, 507 mmol) and ethylene glycol (300 ml) was passed dry HCl gas for 1 hr. During HCl gas bubbling the temperature rose to 60° C. The crude reaction mass was poured onto ice (2 Kg). Crude 41 was filtered, dried and purified by column chromatography on silica gel using hexane:ethyl acetate (95:5) to give pure 41 (70 g, 57.4%) as a white powder. M.p: 73.5-75.5° C.

Workup

  1. customfor 1 hr
  2. customDuring HCl gas bubbling the temperature
  3. customrose to 60° C
  4. customThe crude reaction mass
  5. additionwas poured onto ice (2 Kg)
  6. filtrationCrude 41 was filtered
  7. customdried
  8. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-72fa24f55180422b8c72418d9d6b95cd
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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