Methanol → Methyl 2-chloro-5-methoxy-4-nitrobenzoate

HRID 1019768Notes

Reaction equation

HRID 1019768 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:21]O>>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([O:6][CH3:21])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 580563702-Chloro-5-methoxy-4-nitrobenzoic acid

Product 1

HCID 67465993Methyl 2-chloro-5-methoxy-4-nitrobenzoateYield 71%

Procedure

A solution of 2-chloro-5-methoxy-4-nitrobenzoic acid (1 mmol) and concentrated sulfuric acid (0.02 mmol) in methanol (200 mL) was heated to reflux for 42 hours. The solvents were evaporated under reduced pressure then the residue partitioned between EtOAc (25 mL) and water (25 mL). The separated aqueous phase was extracted with EtOAc (3×25 mL), then the combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (71%) as a solid.

Workup

  1. temperatureto reflux for 42 hours
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue partitioned between EtOAc (25 mL) and water (25 mL)
  4. extractionThe separated aqueous phase was extracted with EtOAc (3×25 mL)
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3c0aea2e8f442948cbd6ab9ff921168
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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