Methyl 4-Formylbenzoate → HCID 10636688, compound

HRID 926018Notes

Reaction equation

HRID 926018 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-8cd959203ab34c1d89b8358f7cf34f93
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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