Sulfuric Acid → 2-(3-Carboxymethyl-4-nitrophenyl)propionic acid

HRID 1873230Notes

Reaction equation

HRID 1873230 reaction equation
S(=O)(=O)(O)O.C([CH:8]([C:30]([O:32]CC)=[O:31])[C:9]1[CH:10]=[C:11]([C:18](C)([C:24](OCC)=O)[C:19]([O:21]CC)=[O:20])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])#N>C(O)(=O)C.O>[C:30]([CH2:8][C:9]1[CH:10]=[C:11]([CH:18]([CH3:24])[C:19]([OH:21])=[O:20])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 18688664HCID 18688664, compound

Product 1

HCID 186886652-(3-Carboxymethyl-4-nitrophenyl)propionic acidYield 75%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

In acetic acid (1 mL) was dissolved diethyl 2-[3-[cyano(ethoxycarbonyl)methyl]-4-nitrophenyl]-2-methylmalonate (obtained in the same manner as in Example 5, 406 mg, 1 mmol.). The solution was heated for 36 hours under reflux, after addition of water (0.9 mL) and concentrated sulfuric acid (0.1 mL). The reaction mixture was diluted with water, and then extracted with ethyl acetate. The ethyl acetate portion was washed successively with water and an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, to give 189 mg (yield: 75%) of the desired compound as a brown crystalline product.

Workup

  1. customobtained in the same manner as in Example 5, 406 mg, 1 mmol
  2. temperatureThe solution was heated for 36 hours
  3. temperatureunder reflux
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate portion was washed successively with water
  6. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3f3d3f0aee314d63b4e08d36aa4c27da
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

Loading…