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

HRID 450080Notes

Reaction equation

HRID 450080 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+]>>[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

3

Reactant 2

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

Product 1

HCID 2841632-Methoxy-5-nitrobenzoic acidYield 87%

Procedure

2-Chloro-5-nitro-benzoic acid (3 g, 14 mmol) was added to a solution of freshly prepared sodium methoxide (from sodium (1.36 g, 56 mmol) in dry methanol (15 ml)) and the reaction was heated to reflux for 12 hr. Methanol was evaporated and the reaction mass diluted with water (25 ml). Conc hydrochloric acid was added until the pH was ˜2. The reaction mixture was stirred at room temperature for 30 min, then the precipitate was filtered and washed with water. Drying at 60-70° C. yielded 2-methoxy-5-nitro benzoic acid (2.4 g, 81%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 12 hr
  3. customMethanol was evaporated
  4. additionthe reaction mass diluted with water (25 ml)
  5. additionConc hydrochloric acid was added until the pH was ˜2
  6. filtrationthe precipitate was filtered
  7. washwashed with water
  8. customDrying at 60-70° C.

Sources & evidence

ORD record
ord-c28a0ce40e1f4638a81ec7db09207937
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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