Nitric Acid → 2-(3-Nitro-4-hydroxyphenyl)propionic acid

HRID 328168Notes

Reaction equation

HRID 328168 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C>[N+:13]([C:7]1[CH:6]=[C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:4]=[CH:3][C:2]=1[OH:1])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1025262-(4-Hydroxyphenyl)propionic acid

Product 1

HCID 128726092-(3-Nitro-4-hydroxyphenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a mixture of 8ml of nitric acid and 15ml of acetic acid 1g of 2-(4-hydroxyphenyl)propionic acid was added and stirred at -10° to -20° C for 4 hours. The reaction mixture was poured into ice water and extracted with chloroform. The extract was washed with a sodium hydrogen carbonate solution and water and then dried over magnesium sulfate. The chloroform solution was concentrated to give crystals, which were recrystallized from water. Yield, 700 mg (58%).

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. washThe extract was washed with a sodium hydrogen carbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe chloroform solution was concentrated
  6. customto give crystals, which
  7. customwere recrystallized from water
  8. customYield

Sources & evidence

ORD record
ord-16d35736b377437ea2d12f3f84d50f0b
Source dataset
uspto-grants-1977_04
Patent number
US04016193

Reaction notes

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