Benzyl Bromide → Benzene, [[(12-bromododecyl)oxy]methyl]-

HRID 1367768Notes

Reaction equation

HRID 1367768 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>C1COCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13789512-Bromo-1-dodecanol

Product 1

HCID 11100339Benzene, [[(12-bromododecyl)oxy]methyl]-Yield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

12-Bromododecan-1-ol (1.83 g) was dissolved in 7 ml of dried THF, and sodium hydride (331.2 mg) was added to this solution. The reaction mixture was stirred at room temperature for 30 minutes, then benzyl bromide (0.99 ml) was added using a syringe, and the reaction mixture was refluxed for 24 hours while stirring. Saturated ammonium chloride solution was added to the reaction mixture, which was then extracted with diethyl ether. The organic layer was washed with saline solution, dried over magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (hexane:dichloromethane=8:2) gave 1-((12-bromododecanoxy)methyl)benzene as a colorless oil at a 73% yield.

Workup

  1. temperaturethe reaction mixture was refluxed for 24 hours
  2. stirringwhile stirring
  3. extractionwas then extracted with diethyl ether
  4. washThe organic layer was washed with saline solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off under reduced pressure
  8. customPurification of the residue by silica gel flash chromatography (hexane:dichloromethane=8:2)

Sources & evidence

ORD record
ord-d7bb9c06732b431d94ea8e06249d7b81
Source dataset
uspto-grants-2011_02
Patent number
US07893304B2

Reaction notes

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