Hydrochloric Acid → 2,5-Bis-(10-hydroxydecoxy)terephthalic acid

HRID 378500Notes

Reaction equation

HRID 378500 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:48])[C:7]1[CH:17]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29]C(=O)C)[C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][C:8]=1[O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:44]C(=O)C)C.Cl>O.C(O)C>[OH:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][O:33][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][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])=[CH:17][C:7]=1[C:6]([OH:48])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19354086Diethyl-2,5-bis-(10-acetoxydecoxy)terephthalate

Product 1

HCID 193540842,5-Bis-(10-hydroxydecoxy)terephthalic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 20.0 g (303 mmol) 85% aqueous KOH in 200 ml water is added to 38.0 g (58.4 mmol) diethyl-2,5-bis-(10-acetoxydecoxy)terephthalate in 200 ml ethanol and the whole is heated under reflux for 1.5 hours. 28.0 ml conc. HCl are then added dropwise with ice-cooling and stirring until the solution shows an acidic pH. The precipitated, colourless crude product is filtered off, washed neutral and recrystallized from ethanol and methanol/acetone.

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooling
  4. filtrationThe precipitated, colourless crude product is filtered off
  5. washwashed neutral
  6. customrecrystallized from ethanol and methanol/acetone

Sources & evidence

ORD record
ord-0261dc4412834aa6b2f1b69ea546e9a6
Source dataset
uspto-grants-2000_02
Patent number
US06031015

Reaction notes

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