Sodium Iodide → Diethyl-2,5-bis-(6-bromohexoxy)terephthalate

HRID 378495

Reaction equation

HRID 378495 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][Br:26].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][Br:26])[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][Br:26])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 79980Diethyl 2,5-dihydroxyterephthalate

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

25.4 g (0.1 mol) diethyl-2,5-dihydroxyterephthalate, 232 ml (1.5 mol) 1,6-dibromohexane, 130 g (0.94 mol) K2CO3 and 200 mg NaI in 200 ml acetone are heated under reflux for 12 hours. The initially yellow suspension decolorizes. After distilling off the solvent, 1200 ml diethyl ether are added to the reaction mixture and the whole is washed twice, each time with 200 ml water. The organic phase is then dried over Na2SO4 and the solvent is distilled off. The colourless product which crystallized out after adding 250 ml petroleum ether at -20° C. is recrystallized once from petroleum ether and twice from ethanol.

Workup

  1. temperatureunder reflux for 12 hours
  2. distillationAfter distilling off the solvent, 1200 ml diethyl ether
  3. additionare added to the reaction mixture
  4. washthe whole is washed twice
  5. dry with materialThe organic phase is then dried over Na2SO4
  6. distillationthe solvent is distilled off
  7. customThe colourless product which crystallized out
  8. additionafter adding 250 ml petroleum ether at -20° C.
  9. customis recrystallized once from petroleum ether and twice from ethanol

Sources & evidence

ORD record
ord-461349af919d48dbbb5d7547acb37497
Source dataset
uspto-grants-2000_02
Patent number
US06031015

Linked notes

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