Methyl 4-Formylbenzoate → HCID 10636688, compound

HRID 1025406Notes

Reaction equation

HRID 1025406 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8]P(=O)(OCC)OCC)=[CH:6][CH:5]=1)([O-:3])=[O:2].C[O-].[Na+].[CH:22]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)=O>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7](/[CH:8]=[CH:22]/[C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)=[CH:17][CH:18]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 256065Diethyl 4-nitrobenzylphosphonateHCID 10942334Sodium Methoxide

Product 1

HCID 10636688HCID 10636688, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a mixture of 50.3 g of diethyl (4-nitrobenzyl)phosphonate and 500 mL of methanol was added dropwise a solution of sodium methylate in methanol (ca. 5 mol/L, 73.7 mL) under ice-cooling, followed by stirring for 30 minutes under ice-cooling. To the reaction mixture was added dropwise a mixture of 30.6 g of methyl 4-formylbenzoate and 300 mL of methanol for 1 hour under ice-cooling, followed by stirring at room temperature for 15 hours after the addition dropwise. The precipitate was collected by filtration to obtain 48.8 g of methyl 4-[(E)-2-(4-nitrophenyl)vinyl]benzoate as a yellow solid. EI: 283

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionTo the reaction mixture was added dropwise
  4. temperaturecooling
  5. stirringby stirring at room temperature for 15 hours
  6. additionafter the addition dropwise
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-80b308119e234c73b594bda4afdd44dd
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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