Water → Ethyl 2-(4-nitrophenyl)propionate

HRID 1704393Notes

Reaction equation

HRID 1704393 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 of ethyl 4-nitrophenylacetate in 350 ml dimethylformamide-toluene (1:1), 9.5 g of 50% 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-4ad32f528cc14e0395f9a9533627f145
Source dataset
uspto-grants-1978_11
Patent number
US04126691

Reaction notes

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