Hydroquinone → 1,4-dihexyloxybenzene

HRID 983571Notes

Reaction equation

HRID 983571 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[CH2:9](Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Na+].[I-]>C(O)C>[CH2:9]([O:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:7][CH2:8][CH2:1][CH2:3][CH2:4][CH3:5])=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 5238Sodium IodideHCID 81011-Bromohexane

Product 1

HCID 43511781,4-dihexyloxybenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon atmosphere, 6.90 g (300 mmol) of Na is reacted with 200 ml of absolute ethanol. Then, 16.5 g (150 mmol) of hydroquinone 5 is added, followed by 42.2 ml (300 mmol) of hexylbromide and 200 mg of anhydrous NaI. The mixture is refluxed overnight. Ethanol is evaporated under reduced pressure and water (150 ml) is added. The product is extracted with dichloromethane and dried over MgSO4. After filtration, the solvents are removed and the crude compound is recrystallized from ethanol.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. customEthanol is evaporated under reduced pressure and water (150 ml)
  3. additionis added
  4. extractionThe product is extracted with dichloromethane
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvents are removed
  8. customthe crude compound is recrystallized from ethanol

Sources & evidence

ORD record
ord-b267670f34114592ad36800ae4fd32a8
Source dataset
uspto-grants-2005_03
Patent number
US06864347B2

Reaction notes

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