Ethylene Glycol → 6-(4-Nitrophenoxy)hexanoic acid 2-hydroxyethyl ester

HRID 1098724Notes

Reaction equation

HRID 1098724 reaction equation
Cl.[N+:2]([C:5]1[CH:19]=[CH:18][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:20](O)[CH2:21][OH:22]>>[OH:22][CH2:21][CH2:20][O:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric Acid2×HCID 223889056-(4-Nitrophenoxy)hexanoic acid

Product 1

HCID 592539506-(4-Nitrophenoxy)hexanoic acid 2-hydroxyethyl ester

Procedure

Dry HCl gas was passed through a mixture of 6-(4-nitrophenoxy)-hexanoic acid 35 (50 g, 197.62 mmol) and ethylene glycol (200 ml) was passed dry HCl gas for one hour. During HCl gas bubbling the temperature rose to 60° C. The crude reaction mass was poured onto ice (1 kg), extracted in to ethyl acetate, washed with water (2×250 ml), dried over sodium sulphate and distilled to get crude 36, which was purified by column chromatography on silica gel using benzene as eluant to get pure 36 (46 g, 78.3) as a light yellow syrup.

Workup

  1. customfor one hour
  2. customDuring HCl gas bubbling the temperature
  3. customrose to 60° C
  4. customThe crude reaction mass
  5. additionwas poured onto ice (1 kg)
  6. extractionextracted in to ethyl acetate
  7. washwashed with water (2×250 ml)
  8. dry with materialdried over sodium sulphate
  9. distillationdistilled
  10. customto get crude 36, which
  11. customwas purified by column chromatography on silica gel
  12. customto get pure 36 (46 g, 78.3) as a light yellow syrup

Sources & evidence

ORD record
ord-9fd557c7054e44f3a32bb5c7c6443b59
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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