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Sodium Hydroxide → 2-(2-Chloro-4-nitrophenyl)acetic acid

HRID 1454693
Notes
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Reaction equation

HRID 1454693 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11](C(OCC)=O)[C:12]([O:14]CC)=[O:13].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21875913Diethyl 2-(2-chloro-4-nitrophenyl)malonate

Product 1

HCID 125105882-(2-Chloro-4-nitrophenyl)acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of diethyl 2-(2-chloro-4-nitrophenyl)malonate (step 1, 7.6 g, 24.2 mmol) in methanol (18 ml) was added 6M-NaOH (12 ml) and stirred for 1 h at 50° C. The reaction was quenched by the addition of saturated citric acid aqueous solution (16 ml) and water. The organic layer was extracted with ethyl acetate (2×50 ml), washed with brine, dried (MgSO4) and concentrated to give 4.52 g (87%) of title compound as light yellow solid.

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Workup

  1. customThe reaction was quenched by the addition of saturated citric acid aqueous solution (16 ml) and water
  2. extractionThe organic layer was extracted with ethyl acetate (2×50 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-44fdfd97d3634a0ca0c7a2ba4e918246
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07479564B2

Reaction notes

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