Water → Methyl 2-(4-nitrophenoxy)propanoate

HRID 1078005Notes

Reaction equation

HRID 1078005 reaction equation
Br[CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionate

Product 1

HCID 4501947Methyl 2-(4-nitrophenoxy)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-bromopropionate (60.12 g, 0.36 mol) is added to a mixture of 4-nitrophenol (25 g, 0.18 mol) and potassium carbonate (49.75 g, 0.36 mol) in acetonitrile. The reaction mixture is refluxed for 18 hours, cooled and poured into water. The phases are separated and the aqueous phase is extracted with ethyl acetate. The organic phase and the organic extracts are combined, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as a white powder, mp 79°-80° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. temperaturecooled
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8af480f5897474ea819acf19106eff0
Source dataset
uspto-grants-1996_08
Patent number
US05545742

Reaction notes

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