Hydrochloric Acid → 4-(4-Chloro-2-nitrophenoxy)benzoic acid

HRID 883896Notes

Reaction equation

HRID 883896 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:19]([O-:21])=[O:20])[CH:3]=1.[Li+].[OH-].Cl>CO>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=2)=[C:4]([N+:19]([O-:21])=[O:20])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 9280984Methyl 4-(4-chloro-2-nitrophenoxy)benzoate

Product 1

HCID 24422524-(4-Chloro-2-nitrophenoxy)benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound from Example 34a (29.6 g, 96.2 mmol) in 200 mL of MeOH was treated with aqueous LiOH (1 M) and heated under reflux for 1 hour. Cooled to room temperature and acidified with aqueous HCl (1 M). Precipitate was filtered, washed with H2O and air-dried giving the title compound as a yellow solid (28.2 g, 100%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. filtrationPrecipitate was filtered
  4. washwashed with H2O
  5. customair-dried

Sources & evidence

ORD record
ord-483264d12f1d475791adcace31aee041
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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