4-Methoxybenzaldehyde → p-METHOXY-alpha-METHYLCINNAMALDEHYDE

HRID 1018467Notes

Reaction equation

HRID 1018467 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH:11]([C:13](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:14])=[O:12]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:13]([CH3:14])[CH:11]=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 42809872-(Triphenylphosphoranylidene)propionaldehyde2×

Product 1

HCID 228993p-METHOXY-alpha-METHYLCINNAMALDEHYDE

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 4-methoxybenzaldehyde (10 g, 0.073 mol) and α-formylethylidenetriphenylphosphorane (25.7 g, 0.081 mol) in dried toluene (200 ml)was heated with stirring at reflux under an atmosphere of nitrogen for 24 h. The cooled reaction mixture was decanted to removed insoluble material and evaporated to give a brown oil. The oil was taken up in diethylether and the resulting suspension purified on flash silica eluting with hexane-diethyl ether (3:2). The resulting oil was a mixture of required product and 4-methoxybenzaldehyde and therefore dissolved in dried toluene (150 ml) and reaction continued as described above with α-formylethylidenetriphenylphosphorane (5.76 g, 0.018 ml) for 7 h. Following the work up and chromatography as above 3-(4-methoxyphenyl)-2-methylpropenaldehyde was obtained as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of nitrogen for 24 h
  3. customThe cooled reaction mixture
  4. customwas decanted
  5. customto removed insoluble material
  6. customevaporated
  7. customto give a brown oil
  8. customthe resulting suspension purified on flash silica eluting with hexane-diethyl ether (3:2)
  9. additiona mixture of required product and 4-methoxybenzaldehyde
  10. dissolutiondissolved in dried toluene (150 ml)
  11. customreaction continued

Sources & evidence

ORD record
ord-4fea7ee6dbb645a8bf40f2145fab96eb
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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