Hydrochloric Acid → Methyl 3-methoxy-5-nitrobenzoate

HRID 2071009Notes

Reaction equation

HRID 2071009 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+]([O-])=O)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2].[O:17]([CH3:19])[Li].Cl>CO>[CH3:19][O:17][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 222067Methyl 3,5-dinitrobenzoateHCID 178419045HCID 178419045, compound

Product 1

HCID 877382Methyl 3-methoxy-5-nitrobenzoateYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

methyl 3,5-dinitrobenzoate (1.5 g, 6.63 mmol, 1 eq) in 10 ml anhydrous MeOH under Ar was heated to reflux at 85° C. LiOMe (1.0 M in MeOH, 13.3 ml, 13.3 mmol, 2 eq) was added to the refluxing solution. After 4 h the reaction was cooled to room temperature, and the mixture was adjusted to pH {tilde over ( )} 3 with concentrated HCl. The solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.7705 g (3.70 mmol, 56% yield) of methyl 3-methoxy-5-nitrobenzoate.

Workup

  1. temperatureAfter 4 h the reaction was cooled to room temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1)
  5. dry with materialdried over Na2SO4
  6. filtrationThe inorganics were filtered off
  7. customthe solvent was removed in vacuo
  8. customPurification via flash chromatography

Sources & evidence

ORD record
ord-f256faa2614445c2b97dff0ff7eff2d1
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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