Bromide ion → 4-Phenoxystyrene

HRID 1781160Notes

Reaction equation

HRID 1781160 reaction equation
[Br-].[CH3:2]C(C)([O-])C.[K+].[O:8]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1.CCCCCC>[O:8]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH2:2])=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 259Bromide ionHCID 661394-PhenoxybenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 786714-Phenoxystyrene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a suspension of methyltriphenylphosphium bromide (7.85 g, 22 mmol) in THF (10 mL) was added potassium tert-butoxide (1.0M solution in THF, 22 mL). After 30 minutes, 4-phenoxybenzaldehyde (3.96 g, 20 mmol) was added to the above mixture. The reaction was diluted with equal volume of hexane after 20 minutes and filtered through silica gel. The residue was rinsed and washed with 20% ether in hexane. Concentration of the filtrate gave the crude product as an off white solid which was used without further purification.

Workup

  1. filtrationfiltered through silica gel
  2. washThe residue was rinsed
  3. washwashed with 20% ether in hexane

Sources & evidence

ORD record
ord-bdaa0213a3154c3a8a7f150b0134379b
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

Loading…