Methanol → Methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate

HRID 1038851Notes

Reaction equation

HRID 1038851 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][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:24]O>>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH:14]([CH3:18])[C:15]([O:17][CH3:24])=[O:16])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 662222213-(2,4-Dinitrophenyl)-2-methylpropanoic acid

Product 1

HCID 86665113Methyl 3-(2,4-dinitrophenyl)-2-methylpropanoateYield 81%

Procedure

To a solution of 3-(2,4-dinitrophenyl)-2-methylpropanoic acid (1.6 g, 5.0 mmol) in MeOH (10 mL) was added H2SO4 (0.85 mL, 16 mmol) and the mixture was heated to reflux overnight. The solvent was removed under reduced pressure and the residue was dissolved in DCM (100 mL). The organic solution was washed with saturated aqueous NaHCO3 and the layers were separated. The organic solution was dried over anhydrous Na2SO4 and filtered. The organic solution was directly purified by preparative TLC (1.0 mm plate), eluting with 5:1 pet ether/EtOAc to give methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate (1.1 g, 81%): LC/MS (Table 2, Method f) Rt=1.95 min; MS m/z: 267 (M−H)−.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (100 mL)
  5. washThe organic solution was washed with saturated aqueous NaHCO3
  6. customthe layers were separated
  7. dry with materialThe organic solution was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customThe organic solution was directly purified by preparative TLC (1.0 mm plate)
  10. washeluting with 5:1 pet ether/EtOAc

Sources & evidence

ORD record
ord-5442342fc5eb4875bce3090f13f43747
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

Loading…