1-Bromohexane → 2,6-Dibromo-1,5-bis(hexyloxy)naphthalene

HRID 645306Notes

Reaction equation

HRID 645306 reaction equation
[O-][CH2:2][CH3:3].[Na+].[Br:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:17])[C:12]=2[OH:16])[C:7]=1[OH:18].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[Br:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:17])[C:12]=2[O:16][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:7]=1[O:18][CH2:15][CH2:6][CH2:7][CH2:8][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 962601,5-Naphthalenediol, 2,6-dibromo-HCID 2723922Sodium ethoxide

Product 1

HCID 183321032,6-Dibromo-1,5-bis(hexyloxy)naphthaleneYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under an inert atmosphere, sodium ethoxide (2.76 g, 40.6 mmol) and 2,6-dibromo-1,5-di hydroxynaphthalene (5 g, 15.7 mmol) were dissolved in ethanol (60 ml). Under reflux, ethanol solution (10 ml) of hexylbromide (6.7 g, 40.6 mmol) was added dropwise in 10 minutes. It was refluxed for 5 hours and then left for cooling. The reaction mixture was added to 1N sodium-hydroxide aqueous solution, and the depositing precipitate was filtrated. The precipitate was washed with methylene chloride, and the washed solution was concentrated under a reduced pressure to obtain a crude product. The desired product was obtained after purifying by silica gel chromatography (toluene:hexane=4:1).

Workup

  1. temperatureUnder reflux
  2. temperatureIt was refluxed for 5 hours
  3. waitleft
  4. temperaturefor cooling
  5. additionThe reaction mixture was added to 1N sodium-hydroxide aqueous solution
  6. filtrationthe depositing precipitate was filtrated
  7. washThe precipitate was washed with methylene chloride
  8. concentrationthe washed solution was concentrated under a reduced pressure
  9. customto obtain a crude product

Sources & evidence

ORD record
ord-1fec327efe3a452790a109fd95f209c2
Source dataset
uspto-grants-2010_04
Patent number
US07701129B2

Reaction notes

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