Benzyl Alcohol → ((4-Bromobutoxy)methyl)benzene

HRID 344244Notes

Reaction equation

HRID 344244 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.O>O1CCCC1>[CH2:3]([O:10][CH2:15][CH2:14][CH2:13][CH2:12][Br:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 80561,4-DibromobutaneHCID 24758Sodium hydride

Product 1

HCID 4422181((4-Bromobutoxy)methyl)benzeneYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% Sodium hydride (1.2 g) was suspended in tetrahydrofuran (30 ml), and benzyl alcohol (3.0 g) was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 min, and again ice-cooled. 1,4-Dibromobutane (6.0 g) was added and the mixture was stirred for 3 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure to give 3.8 g of 4-benzyloxybutyl bromide.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. temperatureagain ice-cooled
  4. stirringthe mixture was stirred for 3 hr
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. customdried
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-89b52cc0d0794006be211b216e20e7b5
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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