Potassium Hydroxide → 2,5-Bis-(6-hydroxyhexoxy)terephthalic acid

HRID 378497Notes

Reaction equation

HRID 378497 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:40])[C:7]1[CH:17]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25]C(=O)C)[C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][C:8]=1[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36]C(=O)C)C>O.C(O)C>[OH:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][C:8]1[CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])=[CH:17][C:7]=1[C:6]([OH:40])=[O:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19354093Diethyl-2,5-bis-(6-acetoxyhexoxy)terephthalate

Product 1

HCID 193540872,5-Bis-(6-hydroxyhexoxy)terephthalic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 25.0 g (379 mmol) 85% KOH in 300 ml water is added to 40.0 g (74.3 mmol) diethyl-2,5-bis-(6-acetoxyhexoxy)terephthalate in 250 ml ethanol and the whole is heated under reflux for 1.5 hours. After distilling off approx. 150 ml ethanol, the reaction mixture is acidified by adding 40.0 g conc. HCl and stored at 2° C. for 20 hours for complete crystallization of the crude product. The colourless crude product is then filtered off, washed neutral with water and recrystallized from ethanol.

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux for 1.5 hours
  3. distillationAfter distilling off approx. 150 ml ethanol
  4. additionby adding 40.0 g conc. HCl
  5. customstored at 2° C. for 20 hours for complete crystallization of the crude product
  6. filtrationThe colourless crude product is then filtered off
  7. washwashed neutral with water
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e6d408f1996043e69a3e2d15a8818465
Source dataset
uspto-grants-2000_02
Patent number
US06031015

Reaction notes

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