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Hydrochloric Acid → 2-Hydroxy-3-nitro-5-trifluoromethylbenzoic acid

HRID 28247
Notes
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Reaction equation

HRID 28247 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C[OH:19].[OH-].[Na+].Cl>[Cl-].C([N+](CC)(CC)CC)C.O>[OH:19][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 100844572-chloro-3-nitro-5-(trifluoromethyl)benzoic Acid

Product 1

HCID 233399522-Hydroxy-3-nitro-5-trifluoromethylbenzoic acid

Reagents, catalysts & solvents 2

HCID 5946
Tetraethylammonium Chloride
Catalyst
HCID 962WaterSolvent

Procedure

27 g of 2-chloro-3-nitro-5-trifluoromethyl-benzoic acid and 1 g of tetraethylammonium chloride are initially introduced into 200 ml of methanol, and 70 g of 50% strength sodium hydroxide solution are added dropwise, whilst stirring. The mixture is subsequently stirred at 65° C. for 5 hours, diluted with 300 ml of H2O and then rendered acid with hydrochloric acid. The solid product is filtered off and recrystallised from water. 16 g of 2-hydroxy-3-nitro-5-trifluoromethylbenzoic acid with the melting point: 166° to 168° C. are obtained.

Workup

  1. additionare added dropwise
  2. stirringThe mixture is subsequently stirred at 65° C. for 5 hours
  3. filtrationThe solid product is filtered off
  4. customrecrystallised from water

Sources & evidence

ORD record
ord-fd2f6a8cbede49f6b17762a83d57156c
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04225731

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes