2-Chloro-5-nitrobenzoic acid → 2-Methoxy-5-nitrobenzoic acid

HRID 59240

Reaction equation

HRID 59240 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][O-:15].[Na+]>CO>[CH3:14][O:15][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 172872-Chloro-5-nitrobenzoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 2841632-Methoxy-5-nitrobenzoic acidYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-5-nitrobenzoic acid (3.0 g, 0.14 mol) in methanol (500 mL) was added sodium methoxide (28.1 g, 0.520 mol). The reaction mass was refluxed for 15 h. Excess of solvent was removed under vacuum and the reaction mass was diluted with water and acidified with dilute HCl to obtain solid which was filtered off to afford 25.0 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.96 (s, 3H), 7.36 (d, J=9.3 Hz, 1H), 8.37 (d, J=9.0 Hz, 1H), 8.45 (s, 1H), 13.32 (br s, 1H)); MS (m/z): 198.25 (M+H)+.

Workup

  1. temperatureThe reaction mass was refluxed for 15 h
  2. customExcess of solvent was removed under vacuum
  3. additionthe reaction mass was diluted with water
  4. customto obtain solid which
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-ede7adb126d54e5e874580fb043060c3
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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