Sodium Hydroxide → 2-(Carboxymethyl)-4-nitrobenzoic acid

HRID 217292Notes

Reaction equation

HRID 217292 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[CH:15](C(OC)=O)[C:16]([O:18]C)=[O:17])([OH:5])=[O:4]>O.CO.C(OCC)(=O)C>[C:16]([CH2:15][C:7]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:6]=1[C:3]([OH:5])=[O:4])([OH:18])=[O:17]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 105900782-(1,3-Dimethoxy-1,3-dioxopropan-2-yl)-4-nitrobenzoic acid

Product 1

HCID 71720252-(Carboxymethyl)-4-nitrobenzoic acidYield 23.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium hydroxide (5.0 g, 125 mmol) in water (60 mL) was added to a solution of dimethyl 2-(2-carboxy-5-nitrophenyl)malonate (7.0 g, 21.5 mmol) in methanol (60 mL) at room temperature. After the reaction solution was stirred at room temperature for 3 hours, methanol was distilled off. The resulting residue was acidified using 1N hydrochloric acid (11 mL). The suspension was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. After the crude product was stirred in ethyl acetate (20 mL) at 70 to 80° C. overnight, the temperature was allowed to return to room temperature. The precipitate was collected by filtration, and dried under reduced pressure to give the title compound (1.13 g, 23%).

Workup

  1. distillationmethanol was distilled off
  2. extractionThe suspension was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude product
  7. customto return to room temperature
  8. filtrationThe precipitate was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-df486528467a40439168e9efa63e6064
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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