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

HRID 2169736Notes

Reaction equation

HRID 2169736 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH2:20](O)[CH2:21][OH:22]>>[OH:22][CH2:21][CH2:20][O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:18][CH:17]=1

Participants

4

Reactant 3

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

Product 1

HCID 592539506-(4-Nitrophenoxy)hexanoic acid 2-hydroxyethyl esterYield 78.3%

Procedure

To a mixture of 6-(4-nitrophenoxy)hexanoic acid 53 (50 g, 197.62 mmol) and ethylene glycol (200 ml) was passed dry HCl gas for one hr. During HCl gas bubbling the temp. rose to 60° C. The crude reaction mass was poured onto ice (1 Kg), extracted into ethyl acetate, washed with water (2×250 ml), dried over sodium sulphate and distilled to get crude 54, which was purified by column chromatography on silica gel using benzene as eluant to get pure 54 (46 g, 78.3%) as a light yellow syrup.

Workup

  1. customfor one hr
  2. customDuring HCl gas bubbling the temp
  3. customrose to 60° C
  4. customThe crude reaction mass
  5. additionwas poured onto ice (1 Kg)
  6. extractionextracted into ethyl acetate
  7. washwashed with water (2×250 ml)
  8. dry with materialdried over sodium sulphate
  9. distillationdistilled
  10. customto get crude 54, which
  11. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-68b226a9f51f4092ad86796270cc4d29
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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