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Benzene → Ethyl 5,5-diphenylpenta-2,4-dienoate

HRID 1007759
Notes
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Reaction equation

HRID 1007759 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([CH:22]=C1CCP(C2C=CC=CC=2)C1(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18].C(O)(=O)C1C=CC=CC=1.C1C=CC=CC=1>CCCCCC>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=[CH:22][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 241BenzeneHCID 243Benzoic AcidHCID 710273,3-DiphenylacroleinHCID 68574662(Carbethoxymethylene)triphenylphospholane

Product 1

HCID 53936700Ethyl 5,5-diphenylpenta-2,4-dienoateYield 82.4%

Reagents, catalysts & solvents 1

HCID 8058
Hexane
Solvent

Procedure

β-Phenylcinnamaldehyde (3.36 g), (carbethoxymethylene)triphenylphospholane (5.68 g), and benzoic acid (0.2 g) were added to anhydrous benzene (80 mL), and the mixture was refluxed under stirring for 3.5 hours. Subsequently, the resultant mixture was cooled to room temperature and condensed under reduced pressure. n-Hexane was added to the residue, and the insoluble matter was collected through filtration and washed several times with n-hexane. The filtrate and the resulting wash liquid were combined and condensed under reduced pressure. The product was purified through silica gel column chromatography (silica gel 40 g, eluent; n-hexane:ethyl acetate=50:1), to thereby yield 3.70 g of the product of interest (yield 82.4%).

Workup

  1. temperaturethe mixture was refluxed
  2. customcondensed under reduced pressure
  3. filtrationthe insoluble matter was collected through filtration
  4. washwashed several times with n-hexane
  5. washThe filtrate and the resulting wash liquid
  6. customcondensed under reduced pressure
  7. customThe product was purified through silica gel column chromatography (silica gel 40 g, eluent; n-hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-5e062507c5c34e06be7b61cd6e4e2387
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06797711B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes