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

HRID 1954419Notes

Reaction equation

HRID 1954419 reaction equation
C[O:2][C:3](=[O:21])[CH:4]([C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:18]([OH:20])=[O:19])C(OC)=O.[OH-].[Na+]>CO.O>[C:3]([CH2:4][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:18]([OH:20])=[O:19])([OH:21])=[O:2]

Participants

5

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 102%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(carboxy-5-nitrophenyl)malonic acid dimethyl ester, (25.0 g, 84 mmol) in methanol (200 mL), sodium hydroxide (5 g, 125 mmol) in water (200 mL) was added. After 3 hrs the reaction was complete, the methanol was removed under vacuum, the contents cooled to 0° C. and acidified with concentrated HCl (37 mL). The aqueous layer was extracted twice with ethyl acetate (200 mL then 100 mL), the combined organic layers were dried with magnesium sulfate, most of the solvent removed under vacuum, and methylene chloride (30 mL) was then added. The formed white solid was filtered off and dried to give 19.3 g of product as a white solid, mp 180-82°0 C. IR(KBr) 3080, 3055, 2983, 1707, 1611, 1585, 1516, 1491, 1424, 1358, 1298, 1237 cm-1.

Workup

  1. customthe methanol was removed under vacuum
  2. extractionThe aqueous layer was extracted twice with ethyl acetate (200 mL
  3. dry with material100 mL), the combined organic layers were dried with magnesium sulfate, most of the solvent
  4. customremoved under vacuum, and methylene chloride (30 mL)
  5. additionwas then added
  6. filtrationThe formed white solid was filtered off
  7. customdried

Sources & evidence

ORD record
ord-97275703f5274fe986cc830e60da2579
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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