4-Methoxybenzaldehyde → Methyl 2-[2-(4-methoxyphenyl)ethenyl]benzoate

HRID 970049Notes

Reaction equation

HRID 970049 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][CH:29]=[CH:28][C:7]=1[CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1.C1CN2C(=NCCC2)C1>C(#N)C>[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[CH:8][C:7]2[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=2[C:4]([O:3][CH3:2])=[O:5])=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 10743695{[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromide

Product 1

HCID 69409617Methyl 2-[2-(4-methoxyphenyl)ethenyl]benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 50 ml of acetonitrile were dissolved 4.91 g (10 mmol) of 2-methoxycarbonylbenzyltriphenylphosphonium bromide and 1.77 g (13 mmol) of 4-methoxybenzaldehyde, and 2.48 g (20 mmol) of 1,5-diazabicyclo[4.3.0]-5-nonene was added to the solution and the mixture was refluxed for 5 hours.

Workup

  1. additionwas added to the solution
  2. temperaturethe mixture was refluxed for 5 hours

Sources & evidence

ORD record
ord-b3e670cc92b34ebd97673e10fa08783d
Source dataset
uspto-grants-2007_12
Patent number
US07309718B2

Reaction notes

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