(4-Nitrophenyl)acetic acid → Actarit

HRID 1733016Notes

Reaction equation

HRID 1733016 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C(O)(=O)C.[Fe]>[C:14]([NH:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 4661(4-Nitrophenyl)acetic acidHCID 7918Acetic Anhydride

Product 1

HCID 2018ActaritYield 83.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

150 g (0.83 mole) of 4-nitrophenylacetic acid are heated to 95° C. in 1.5 liters of glacial acetic acid. With vigorous stirring, 160 g (2.86 moles) of iron powder are added in portions in such a manner that the internal temperature does not rise above 105° C. Towards the end of the reaction, the reaction mixture clears up. 200 ml of acetic anhydride are added, and stirring is afterwards continued for a further 30 minutes at 100° C. Cooling to room temperature is allowed to take place; this is followed by suction filtration from formed iron salts, concentration to half the volume, and dilution with 1.5 liters of water. Extraction is effected three times with, in each case, one liter of ethyl acetate. This is followed by washing the organic phase with water and then concentrating it to dryness to obtain 133 g (83.1% of theory) of 4-acetamidophenylacetic acid (m.p. 168° to 170° C.).

Workup

  1. customdoes not rise above 105° C
  2. customTowards the end of the reaction
  3. filtrationthis is followed by suction filtration
  4. customfrom formed
  5. concentrationiron salts, concentration to half the volume, and dilution with 1.5 liters of water
  6. extractionExtraction
  7. washby washing the organic phase with water
  8. concentrationconcentrating it to dryness

Sources & evidence

ORD record
ord-2e0507ef6829474d8cca34dacadc170e
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

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