Sodium Iodide → Diethyl-2,5-bis-(10-bromodecoxy)terephthalate

HRID 378498

Reaction equation

HRID 378498 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:15]=[C:14]([OH:16])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[OH:17])[CH3:2].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:15]=[C:14]([O:16][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[O:17][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 79980Diethyl 2,5-dihydroxyterephthalateHCID 2214831,10-Dibromodecane

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

25.4 g (0.1 mol) diethyl-2,5-dihydroxyterephthalate, 450 g (1.5 mol) 1,10-dibromodecane, 138 g (1.0 mol) K2CO3 and 200 mg NaI in 200 ml acetone are heated under reflux for 28 hours until the originally yellow suspension has decolorized. After distilling off the solvent, the reaction mixture is extracted twice with diethyl ether (2×250 ml), and insoluble salts are filtered off. The filtrate is washed twice with 200 ml water and dried over Na2SO4. The solvent is then distilled off. The colourless, solid residue is washed twice with petroleum ether and then recrystallized from petroleum ether.

Workup

  1. temperatureunder reflux for 28 hours until the originally yellow suspension
  2. distillationAfter distilling off the solvent
  3. extractionthe reaction mixture is extracted twice with diethyl ether (2×250 ml), and insoluble salts
  4. filtrationare filtered off
  5. washThe filtrate is washed twice with 200 ml water
  6. dry with materialdried over Na2SO4
  7. distillationThe solvent is then distilled off
  8. washThe colourless, solid residue is washed twice with petroleum ether
  9. customrecrystallized from petroleum ether

Sources & evidence

ORD record
ord-8771b1594f4a446fb4425ec5b0c79c75
Source dataset
uspto-grants-2000_02
Patent number
US06031015

Linked notes

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