Benzyl Bromide → 1-(Benzyloxy)-4-ethenylbenzene

HRID 1873105Notes

Reaction equation

HRID 1873105 reaction equation
[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=O)[CH3:2].C[N+](C)(C)C.[OH-].C(Br)[C:20]1[CH:25]=[CH:24]C=[CH:22][CH:21]=1>>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)[C:2]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 60966Tetramethylammonium hydroxideHCID 758214-Ethenylphenyl acetate

Product 1

HCID 110529161-(Benzyloxy)-4-ethenylbenzeneYield 81%

Procedure

Approximately 10 gs (6.17×10-2 moles) of 4-acetoxystyrene was added to a 25 wt % solution of TMAH (51 mL). After 15 minutes of stirring a clear yellowish solution was obtained. About 10.6 gs (6.17×10-2 moles) of benzyl bromide was added to this solution with stirring. Slow formation of product crystals was observed. Reaction was complete as seen by thin layer chromatography after about 5 hours. The crystals were filtered-off, washed with distilled water, and sucked dry. In this way, 10.5 gs (81% yield) of pure desired product was obtained. Analysis of the product indicated:

Workup

  1. customwas obtained
  2. stirringwith stirring
  3. customReaction
  4. waitas seen by thin layer chromatography after about 5 hours
  5. washwashed with distilled water
  6. customsucked dry

Sources & evidence

ORD record
ord-e14f2e8882594eb0b8a412f5f4eb3d9c
Source dataset
uspto-grants-2000_08
Patent number
US06111133

Reaction notes

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