4-Phenoxybenzaldehyde → 4-Phenoxystyrene

HRID 1957328Notes

Reaction equation

HRID 1957328 reaction equation
[CH3:1]C(C)([O-])C.[K+].[O:7]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCCCCC>[O:7]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[CH2:1])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 661394-PhenoxybenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 786714-Phenoxystyrene

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a suspension of methyltriphenylphosphonium 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 (80 g). The residue was rinsed and washed with 20% ether in hexane. Concentration of the filtrate in vacuo gave the crude product as an off white solid which was used without further purification.

Workup

  1. filtrationfiltered through silica gel (80 g)
  2. washThe residue was rinsed
  3. washwashed with 20% ether in hexane

Sources & evidence

ORD record
ord-30b34a2cec934224a58a25ca81771f20
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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