Potassium Acetate → Diethyl-2,5-bis-(10-acetoxydecoxy)terephthalate

HRID 378499Notes

Reaction equation

HRID 378499 reaction equation
[CH2:1]([O:3][C:4](=[O:40])[C:5]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br)[CH3:2].[C:41]([O-:44])(=[O:43])[CH3:42].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(#N)C>[CH2:1]([O:3][C:4](=[O:40])[C:5]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:43][C:41](=[O:44])[CH3:42])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:40][C:4](=[O:3])[CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 19354090Diethyl-2,5-bis-(10-bromodecoxy)terephthalate

Product 1

HCID 19354086Diethyl-2,5-bis-(10-acetoxydecoxy)terephthalate

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

46.4 g (67.0 mmol) diethyl-2,5-bis-(10-bromodecoxy)terephthalate, 65.8 g (671 mmol) potassium acetate and 3.4 g (8.5 mmol) Aliquat 336® in 350 ml absolute acetonitrile are heated under N2 under reflux for 48 hours. After distilling off the solvent, the reaction mixture is taken up in 300 ml chloroform, insoluble salts are filtered off and the filtrate is washed twice with 150 ml water. The organic phase is dried over Na2SO4 and the solvent is then distilled off. 300 ml petroleum ether are added to the remaining, oily residue, the product crystallising out after 16 hours at -20° C. It is then recrystallized from ethanol.

Workup

  1. temperatureunder reflux for 48 hours
  2. distillationAfter distilling off the solvent
  3. filtrationinsoluble salts are filtered off
  4. washthe filtrate is washed twice with 150 ml water
  5. dry with materialThe organic phase is dried over Na2SO4
  6. distillationthe solvent is then distilled off
  7. addition300 ml petroleum ether are added to the remaining, oily residue
  8. customthe product crystallising out after 16 hours at -20° C
  9. customIt is then recrystallized from ethanol

Sources & evidence

ORD record
ord-98f4381273a6448eb0452d17566b6ca2
Source dataset
uspto-grants-2000_02
Patent number
US06031015

Reaction notes

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