Benzyl Bromide → Benzene, [(3-butenyloxy)methyl]-

HRID 892718Notes

Reaction equation

HRID 892718 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH:5]=[CH2:6].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[CH2:3]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 693893-Buten-1-ol

Product 1

HCID 10441993Benzene, [(3-butenyloxy)methyl]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.24 g) was slowly added to a solution of 3-buten-1-ol (0.72 g) in DMF (15 ml) at 0° C., and the reaction stirred for 30 minutes. Benzyl bromide (1.9 g) was added and the reaction was stirred at 25° C. for 18 hours. The mixture was filtered and concentrated. The residue was dissolved in hexane, washed with water (3×), dried over MgSO4, and concentrated. Purification by chromatography over silica gel (5% ethyl ether in hexane) afforded the titled compound.

Workup

  1. stirringthe reaction was stirred at 25° C. for 18 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in hexane
  5. washwashed with water (3×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customPurification by chromatography over silica gel (5% ethyl ether in hexane)

Sources & evidence

ORD record
ord-6d5db8413a574664994feed5ea874261
Source dataset
uspto-grants-1992_06
Patent number
US05120729

Reaction notes

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