2-Nitrophenol → Ethyl 4-(2-nitrophenoxy)butanoate

HRID 2248010Notes

Reaction equation

HRID 2248010 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])([O-:5])=[O:4].[CH2:13]([O:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19]Br)[CH3:14]>CN(C)C=O>[CH2:13]([O:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N+:3]([O-:5])=[O:4])[CH3:14]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 12433959Ethyl 4-(2-nitrophenoxy)butanoateYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (16.5 9, content: 62.4%) was suspended in N,N-dimethylformamide (500 ml). 0-nitrophenol (60 g) dissolved in N,N-dimethylformamide (100 ml) was added dropwise into the mixture with stirring in ice-bath over about 20 mins. The mixture was stirred for 1 hr. at a room temperature. 4-bromobutanoic acid ethyl ester (84.2 g) dissolved in N,N-dimethylformamide (200 ml) was added to the mixture. The solution was stirred for 15 hrs at about 70° C. N,N-dimethylformamide was evaporated in vacuo. Ethyl acetate (800 ml) was added to the residue. The mixture was washed with a water and a saturated brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (n-hexane: ethyl acetate =5:1→3:1) to give the title compound (77.3 g) having the following physical data:

Workup

  1. additionwas added dropwise into the mixture
  2. stirringThe mixture was stirred for 1 hr
  3. customat a room temperature
  4. additionwas added to the mixture
  5. stirringThe solution was stirred for 15 hrs at about 70° C
  6. customN,N-dimethylformamide was evaporated in vacuo
  7. additionEthyl acetate (800 ml) was added to the residue
  8. washThe mixture was washed with a water
  9. dry with materiala saturated brine, dried over magnesium sulfate
  10. customevaporated
  11. customThe residue was purified by column chromatography on silica gel (n-hexane: ethyl acetate =5:1→3:1)

Sources & evidence

ORD record
ord-64684ab900a343f1a22ac47670cd1130
Source dataset
uspto-grants-1991_08
Patent number
US05037852

Reaction notes

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