Sodium Hydroxide → 3-Chloro-5-nitrobenzoic acid

HRID 1819799Notes

Reaction equation

HRID 1819799 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([Cl:13])[CH:5]=1.[OH-].[Na+]>CO.O>[Cl:13][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=1)[C:3]([OH:14])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2991916methyl 3-chloro-5-nitrobenzoate

Product 1

HCID 2214843-Chloro-5-nitrobenzoic acidYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-chloro-5-nitro-benzoic acid methyl ester (325, 2.75 g, 12.76 mmol) in 60 mL of MeOH was added a solution of NaOH (EM, 5.10 g, 127.6 mmol) in 35 mL of H2O. The mixture was stirred for 2 h. MeOH was removed under reduced pressure, and the mixture was diluted with water, brought to pH 2 with con. HCl. Filtration followed by washing with water gave 2.35 g (92%) desired product. 1H NMR (400 MHz, DMSO-d6) δ 14.02 (s, 1H), 8.57-8.52 (m, 2H), 8.31 (dd, J=1.9, 1.2 Hz, 1H), 3.94 (s, 3H). MS (EI): m/z 200 (M−H).

Workup

  1. customMeOH was removed under reduced pressure
  2. additionthe mixture was diluted with water
  3. filtrationFiltration
  4. washby washing with water

Sources & evidence

ORD record
ord-e880102652c04fc0829d4f6f0224465c
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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