Methanol → Methyl 2-chloro-4-nitrobenzoate

HRID 1843040Notes

Reaction equation

HRID 1843040 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:19]O>>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 74482-Chloro-4-nitrobenzoic acid

Product 1

HCID 83343Methyl 2-chloro-4-nitrobenzoate

Procedure

To a stirred solution of 2-Chloro-4-nitrobenzoic acid (500 mg, 2.48 mmol) in methanol was added sulfuric acid in catalytic amounts. The mixture was heated to reflux overnight. TLC showed complete consumption of starting material. The reaction mixture was slowly cooled room temperature and neutralized with sodium bicarbonate. The mixture was extracted with EtOAc and washed with water and brine. The extract was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to afford pure compound methyl 2-chloro-4-nitrobenzoate 468 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customconsumption of starting material
  4. customwas slowly cooled room temperature and neutralized with sodium bicarbonate
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with water and brine
  7. dry with materialThe extract was dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e1f776e708094a7ab4b5407cb11b2bbd
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

Loading…