Water → Ethyl 2-(4-nitrophenyl)propionate

HRID 1973557Notes

Reaction equation

HRID 1973557 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:18]I.O>CN(C)C=O.C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 3016550Ethyl 2-(4-nitrophenyl)propionate

Reagents, catalysts & solvents 1

HCID 21735183Dimethylformamide tolueneSolvent

Procedure

To the solution of 52 g ethyl 4-nitrophenylacetate in 350 ml dimethylformamide-toluene (1:1), 9.5 g of 50 percent sodium hydride in mineral oil are added portionwise while stirring and cooling. After 11/2 hours stirring at room temperature, 26 g methyl iodide are added dropwise and the mixture is stirred overnight at room temperature. The mixture is carefully combined with water, extracted with diethyl ether, the extract dried, filtered and evaporated. The residue is taken up in 100 ml ethanol, the solution seeded with a few crystals starting material and allowed to stand in the cold. The precipitate formed is filtered off and the filtrate evaporated, to yield the ethyl α-(4-nitrophenyl)-propionate.

Workup

  1. temperaturecooling
  2. stirringAfter 11/2 hours stirring at room temperature
  3. stirringthe mixture is stirred overnight at room temperature
  4. extractionextracted with diethyl ether
  5. customthe extract dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe precipitate formed
  9. filtrationis filtered off
  10. customthe filtrate evaporated

Sources & evidence

ORD record
ord-bfda9d1adea24b3c80daabaa07f62839
Source dataset
uspto-grants-1976_12
Patent number
US03997669

Reaction notes

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