Methanol → Methyl 2-(2,4-dinitrophenyl)acetate

HRID 887595Notes

Reaction equation

HRID 887595 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=[O:15])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:22]O>>[CH3:22][O:15][C:14](=[O:16])[CH2:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2215132,4-Dinitrophenylacetic acid

Product 1

HCID 286146Methyl 2-(2,4-dinitrophenyl)acetate

Procedure

To a solution of (2,4-dinitro-phenyl)-acetic acid (5 g) in MeOH (100 mL) was added concentrated H2SO4 (1 mL) and the resulting solution was heated at reflux for overnight. After removing solvent in vacuum, the residue was partitioned between EtOAc and aqueous NaHCO3 (sat.). The organic solution was concentrated in vacuum to give the desired compound which was used without further purification.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for overnight
  3. customAfter removing solvent in vacuum
  4. customthe residue was partitioned between EtOAc and aqueous NaHCO3 (sat.)
  5. concentrationThe organic solution was concentrated in vacuum

Sources & evidence

ORD record
ord-b3e380bb17184136974608d232eb1e40
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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