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Sodium Hydroxide → 2-Nitro-5-(2,4,6-trichlorophenoxy)benzoic acid

HRID 894933
Notes
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Reaction equation

HRID 894933 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:17]=2[Cl:24])=[CH:11][C:5]=1[C:6]([O:8]CC)=[O:7])([O-:3])=[O:2].[OH-].[Na+]>C(O)C.O>[N+:1]([C:4]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:17]([Cl:24])=[CH:18][C:19]([Cl:23])=[CH:20][C:21]=2[Cl:22])=[CH:11][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13013678Ethyl 2-nitro-5-(2,4,6-trichlorophenoxy)benzoate

Product 1

HCID 130136912-Nitro-5-(2,4,6-trichlorophenoxy)benzoic acidYield 66.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product from paragraph (a) (6.86 g) in ethanol (50 ml) was heated and stirred with a solution of sodium hydroxide (0.8 g) in water (10 ml) at 60°-70° C. for 4 hours. The mixture was then cooled and the ethanol removed under reduced pressure. The residue was diluted to 100 ml with water and brought to pH 2 with concentrated hydrochloric acid. The solid which separated was collected and recrystallised from toluene to give the required benzoic acid derivative (4.26 g) with a melting point of 192°-192.5° C.

Workup

  1. temperatureThe mixture was then cooled
  2. customthe ethanol removed under reduced pressure
  3. additionThe residue was diluted to 100 ml with water
  4. customThe solid which separated
  5. customwas collected
  6. customrecrystallised from toluene

Sources & evidence

ORD record
ord-0285d12a4b87462aa2c6ac0498018813
Source dataset
uspto-grants-1981_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04285723

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes