Hydrochloric Acid → 3-Hydroxy-2-nitrobenzoic acid

HRID 415161

Reaction equation

HRID 415161 reaction equation
Cl[C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-:14].[K+].Cl>O>[OH:14][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 209023-Chloro-2-nitrobenzoic acid

Product 1

HCID 2932913-Hydroxy-2-nitrobenzoic acidYield 150.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-chloro-2-nitrobenzoic acid (40 g, 0.20 mol) and KOH (160 g, 2.86 mol) in water (200 mL) was heated to reflux for 16 hr. 6N aqueous hydrochloric acid was added to the mixture to pH=3, then extracted with ethyl acetate (500 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 3-hydroxy-2-nitrobenzoic acid (55 g), LC-MS (ESI) m/z 184 [M+1]−.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hr
  3. extractionextracted with ethyl acetate (500 mL×4)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f5de328daff54048ac75d1f6e3803ac8
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Linked notes

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