Sodium Iodide → Diethyl 2,5-bis(hexyloxy)benzene-1,4-dicarboxylate

HRID 378493

Reaction equation

HRID 378493 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][CH3:25].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][CH3:25])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[O:17][CH2:14][CH2:15][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 79980Diethyl 2,5-dihydroxyterephthalate

Product 1

HCID 21958414Diethyl 2,5-bis(hexyloxy)benzene-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

15.0 g (59.0 mmol) diethyl-2,5-dihydroxyterephthalate, 20.0 ml (142 mmol) 1-bromohexane, 28.0 g (203 mmol) K2CO3 and 200 mg NaI in 100 ml acetone are heated under reflux for 66 hours. The initially yellow suspension becomes largely decolorized. The solvent is then distilled off and the residue is taken up in 400 ml ethyl acetate and 200 ml water. After removing the aqueous phase, the organic phase is washed three times with 80 ml 1 N NaOH and three times with 100 ml water and then dried over Na2SO4. After distilling off the ethyl acetate, the residue is taken up in petroleum ether. At -30° C., colourless crystals form which are recrystallized again from petroleum ether.

Workup

  1. temperatureunder reflux for 66 hours
  2. distillationThe solvent is then distilled off
  3. customAfter removing the aqueous phase
  4. washthe organic phase is washed three times with 80 ml 1 N NaOH and three times with 100 ml water
  5. dry with materialdried over Na2SO4
  6. distillationAfter distilling off the ethyl acetate
  7. customAt -30° C., colourless crystals form which are recrystallized again from petroleum ether

Sources & evidence

ORD record
ord-de56d9550e15438e81802b7ca78bf2a5
Source dataset
uspto-grants-2000_02
Patent number
US06031015

Linked notes

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