Potassium Acetate → Diethyl-2,5-bis-(6-acetoxyhexoxy)terephthalate

HRID 378496Notes

Reaction equation

HRID 378496 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br)[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)[CH3:2].[C:33]([O-:36])(=[O:35])[CH3:34].[K+]>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.C(#N)C>[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:35][C:33](=[O:36])[CH3:34])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:32][C:4](=[O:3])[CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 19354089Diethyl-2,5-bis-(6-bromohexoxy)terephthalate

Product 1

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

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

50.0 g (86.0 mmol) diethyl-2,5-bis-(6-bromohexoxy)terephthalate, 84.5 g (861 mmol) potassium acetate and 4.4 g (11 mmol) methyl trioctyl ammonium chloride (Aliquat 336®, tricaprylyl methyl ammonium chloride, Fluka, CAS 5137.55.3) in 500 ml absolute acetonitrile are heated under reflux in a nitrogen atmosphere for 48 hours. After distilling off the solvent, the reaction mixture is taken up in 1200 ml ethyl acetate and washed three times with water (3×300 ml). The organic phase is dried over MgSO4 and the solvent is then distilled off. 1000 ml petroleum ether is added to the residual, oily residue and the product crystallizing out after 16 hours at -20° C. is recrystallized from petroleum ether/ethyl acetate.

Workup

  1. temperatureunder reflux in a nitrogen atmosphere for 48 hours
  2. distillationAfter distilling off the solvent
  3. washwashed three times with water (3×300 ml)
  4. dry with materialThe organic phase is dried over MgSO4
  5. distillationthe solvent is then distilled off
  6. addition1000 ml petroleum ether is added to the residual, oily residue
  7. customthe product crystallizing out after 16 hours at -20° C.
  8. customis recrystallized from petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-139807bff8214104b3c511448b127cac
Source dataset
uspto-grants-2000_02
Patent number
US06031015

Reaction notes

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