2-Phenylpropanal → 1-(4'-Carboxyphenyl)-3-phenyl-trans-1-butene

HRID 845870Notes

Reaction equation

HRID 845870 reaction equation
[H-].[Na+].[Br-].[C:4]([C:7]1[CH:32]=[CH:31][C:10]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:9][CH:8]=1)([OH:6])=[O:5].[C:33]1([CH:39]([CH3:42])[CH:40]=O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.S(=O)(=O)(O)[O-].[Na+]>CS(C)=O>[C:4]([C:7]1[CH:8]=[CH:9][C:10](/[CH:11]=[CH:40]/[CH:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH3:42])=[CH:31][CH:32]=1)([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 71462-PhenylpropanalHCID 24758Sodium hydrideHCID 516919Sodium BisulfateHCID 22675580(4-Carboxybenzyl)triphenylphosphonium bromide

Product 1

HCID 141829521-(4'-Carboxyphenyl)-3-phenyl-trans-1-butene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of sodium hydride (50% in mineral oil; 3.4 g, 70 mmol) and dimethyl sulfoxide (50 ml) was heated to 75° for 1.5 hours under a nitrogen atmosphere. The solution was cooled to ambient temperature, and (4-carboxybenzyl)triphenylphosphonium bromide (18 g, 37 mmol) was added. The resulting red solution was stirred for 1 hour at ambient temperature. A solution of α-phenylpropionaldehyde (2.5 g, 19 mmol) in dimethyl sulfoxide (10 ml) was added over a ten minute period. Stirring was continued for an additional twenty minutes. The reaction mixture was poured into 0.2M sodium bisulfate, and the resulting mixture was extracted three times with ether. The combined ether extracts were washed with saturated aqueous sodium chloride, dried (sodium sulfate) and evaporated. The residue was subjected to column chromatography on silica gel (E. Merck No. 7734). Elution with 1% acetic acid in 1:1 hexane-ether afforded pure 1-(4'-carboxyphenyl)-3-phenyl-trans-1-butene as a white solid; yield 48 mg (10%); m.p. 127°-130°; mass spectrum m/z 252 (M), 237 (M--CH3).

Workup

  1. temperaturewas heated to 75° for 1.5 hours under a nitrogen atmosphere
  2. stirringStirring
  3. waitwas continued for an additional twenty minutes
  4. extractionthe resulting mixture was extracted three times with ether
  5. washThe combined ether extracts were washed with saturated aqueous sodium chloride
  6. dry with materialdried (sodium sulfate)
  7. customevaporated
  8. washElution with 1% acetic acid in 1:1 hexane-ether afforded pure 1-(4'-carboxyphenyl)-3-phenyl-trans-1-butene as a white solid

Sources & evidence

ORD record
ord-4387316caf1541f49ad2825b8d7cee7a
Source dataset
uspto-grants-1988_07
Patent number
US04760161

Reaction notes

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