Benzenepropanal → HCID 5368479, compound

HRID 2248016Notes

Reaction equation

HRID 2248016 reaction equation
[CH:1](=O)[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:13][CH2:14][CH3:15])=[O:12]>C1(C)C=CC=CC=1>[CH2:14]([O:13][C:11](=[O:12])/[CH:16]=[CH:1]/[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:15]

Participants

4

Reactant 2

HCID 7707BenzenepropanalHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 5368479HCID 5368479, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of dihydrocinnamaldehyde (6.73 g, 50.2 mmol) and (carboethoxymethylene)triphenylphosphorane (17.84 g, 50.2 mmol) in toluene (250 mL) was refluxed for 18 h. It was then cooled to r.t and concentrated in vacuo. The residue was taken up in ether (250 mL) and the triphenylphosphine oxide was filtered off. The filtrate was concentrated to afford the intermediate trans-ethyl-(5-phenyl)-2-pentenoate (32.1).

Workup

  1. temperatureIt was then cooled
  2. concentrationconcentrated in vacuo
  3. filtrationthe triphenylphosphine oxide was filtered off
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-379c678873ca42fc949ef43a579bd617
Source dataset
uspto-grants-1991_08
Patent number
US05037853

Reaction notes

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