Vanillin → 1-(4'-Hydroxy,3'-methoxyphenyl)-4-phenyl-1-butene-3-one

HRID 847538Notes

Reaction equation

HRID 847538 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].C1([PH2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)C2C=CC=CC=2)C=CC=CC=1.[O:31](CC(=O)C)[C:32]1[CH:37]=CC=C[CH:33]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:33][C:32](=[O:31])[CH2:37][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:4][C:3]=1[O:10][CH3:11]

Participants

5

Reactant 2

HCID 1183VanillinHCID 178468789HCID 178468789, compound

Product 1

HCID 539208741-(4'-Hydroxy,3'-methoxyphenyl)-4-phenyl-1-butene-3-oneYield 81%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxy-3-methoxybenzaldehyde (2.1 g, 13.8 mMol) and 3-phenoxypropane-2-one triphenylphosphorane (2.8 g, 6.9 mMol) (prepared as described by LeCorre: C. R. Acad. Sci. Paris 273 81 (1971)) are dissolved in 100 ml of toluene and warmed to reflux. After three hours, the solvent is evaporated and the residue is taken up in tHF. Sodium bisulfite (10.0 g) is dissolved in 100 ml of water and stirred with the solution for one hour. The THF is evaporated and the water is extracted with chloroform. Drying over magnesium sulfate and evaporation of the chloroform gives a yellow oil. Flash chromatography in ethyl acetate on silica gel gives 1.5 g (65%) of 1-(4'-hydroxy,3'-methoxyphenyl)-4-phenyl-1-butene-3-one; mp=85°-87° C. C, H analysis: Calcd for C17H16O4 (71.81, 5.68); Found (71.85, 5.50).

Workup

  1. temperaturewarmed to reflux
  2. customthe solvent is evaporated
  3. dissolutionSodium bisulfite (10.0 g) is dissolved in 100 ml of water
  4. customThe THF is evaporated
  5. extractionthe water is extracted with chloroform
  6. dry with materialDrying over magnesium sulfate and evaporation of the chloroform
  7. customgives a yellow oil

Sources & evidence

ORD record
ord-76a03d7971514bcdbf854d0267151164
Source dataset
uspto-grants-1992_08
Patent number
US05142095

Reaction notes

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