Methyl 4-Formylbenzoate → HCID 329156, compound

HRID 1586815Notes

Reaction equation

HRID 1586815 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=O>COCCOC>[CH3:23][O:22][C:20]([C:19]1[CH:24]=[CH:25][C:16]([CH:14]=[CH:3][C:1]#[N:2])=[CH:17][CH:18]=1)=[O:21]

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 329156HCID 329156, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred solution of diethyl cyanomethylphosphonate (96 ml) in 1,2-dimethoxyethane (375 ml) was added sodium hydride (60%: 22g) portionwise below 5° C. and the stirring was continued at 0° C. for half an hour and then at ambient temperature for half an hour. The reaction mixture was recooled to 0° C. and a solution of methyl p-formylbenzoate (75 g) in 1,2-dimethoxyethane (375 ml) was added to the reaction mixture below 6° C. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and diluted with ethyl acetate. The organic layer was washed with water and aqueous saturated sodium bicarbonate and dried over magnesium sulfate and filtered. The solvent was removed in vacuo and the solid product was recrystallized from ethanol to give 4-methoxycarbonylcinnamonitrile (52.12 g) as a white needle.

Workup

  1. waitthe stirring was continued at 0° C. for half an hour
  2. waitat ambient temperature for half an hour
  3. customwas recooled to 0° C.
  4. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  5. additiondiluted with ethyl acetate
  6. washThe organic layer was washed with water and aqueous saturated sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed in vacuo
  10. customthe solid product was recrystallized from ethanol

Sources & evidence

ORD record
ord-37aac32f924a40f3902ea65510df694d
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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