Methanol → Methyl 2-chloro-3-nitrobenzoate

HRID 1398820Notes

Reaction equation

HRID 1398820 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14](Cl)(=O)C(Cl)=O.CO>O1CCCC1>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 198702-Chloro-3-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoateYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-3-nitrobenzoic acid (100 g, 0.496 mol) in tetrahydrofuran (1000 mL) was added dropwise oxalyl chloride (46.8 mL, 0.546 mol) at 0° C., and the mixture was stirred at room temperature for 3 hr. To the mixture was added dropwise methanol (300 mL) at 0° C., and the mixture was stirred at room temperature for 14 hr. The mixture was concentrated and the residue was neutralized with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the solid, which was washed with n-hexane to give the title compound as a yellow powder (103 g, 0.478 mol, 96%).

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hr
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the solid, which
  9. washwas washed with n-hexane

Sources & evidence

ORD record
ord-fd20c70e68ab4a5baf6a9c5b7dfc599f
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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