Nitric Acid → 2-(4-Methoxy-3-nitrophenyl)propanoic acid

HRID 328164

Reaction equation

HRID 328164 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[N+:14]([C:8]1[CH:7]=[C:6]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 257576p-Methoxyphenylpropionic acid

Product 1

HCID 214441642-(4-Methoxy-3-nitrophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5.23g of 2-(4-methoxyphenyl)propionic acid was added gradually under cooling in a mixture of 27.5g of nitric acid and 19.9g of sulfuric acid. After the mixture was stirred at -10° C to -5° C for 6 hours, the mixture was poured into ice-water. The thus obtained oily substance was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled off. The residue was purified by means of silica gel chromatography to give the object compound having m.p. 89° - 90° C in a yield of 5.0g (76%).

Workup

  1. extractionThe thus obtained oily substance was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. distillationdistilled off
  4. customThe residue was purified by means of silica gel chromatography
  5. customto give the object compound

Sources & evidence

ORD record
ord-b476517894b34ed79c4361eb6510c9fe
Source dataset
uspto-grants-1977_04
Patent number
US04016193

Linked notes

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