Benzyl Bromide → (((10-Bromodecyl)oxy)methyl)benzene

HRID 1367765Notes

Reaction equation

HRID 1367765 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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][O:12][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1045071-Decanol, 10-bromo-

Product 1

HCID 13478286(((10-Bromodecyl)oxy)methyl)benzeneYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10-Bromodecan-1-ol (4.6 g) was dissolved in 20 ml of dried THF, and sodium hydride (933.6 mg) was added to this solution. The reaction mixture was stirred at room temperature for 30 minutes, then benzyl bromide (2.78 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-((10-bromodecanoxy)methyl)benzene as a colorless oil at an 88% 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-9dafb52ce69f4882a26aee9c5549d184
Source dataset
uspto-grants-2011_02
Patent number
US07893304B2

Reaction notes

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