Acetic Anhydride → 3-Hydroxy-5-nitro-4-phenylbenzoic acid

HRID 1605547Notes

Reaction equation

HRID 1605547 reaction equation
F[B-](F)(F)F.[C:6]([C:9]1[CH:10]=[C:11]([N+:23]([O-:25])=[O:24])[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([N+]#N)[CH:14]=1)([OH:8])=[O:7].C(OC(=O)C)(=[O:28])C>C(O)(=O)C>[OH:28][C:13]1[CH:14]=[C:9]([CH:10]=[C:11]([N+:23]([O-:25])=[O:24])[C:12]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 215468605-Carboxy-3-nitro-2phenylbenzenediazonium tetrafluoroborate

Product 1

HCID 215468503-Hydroxy-5-nitro-4-phenylbenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Carboxy-3-nitro-2phenylbenzenediazonium tetrafluoroborate (110 g ) is added in portions to a stirred and refluxing mixture of acetic anhydride (275 ml) and acetic acid (275 ml). The mixture is refluxed for a further 4-5 hours and is then poured into ice-water (about 4 liters). The mixture is left for 20 hours, and the precipitated crude 3-acetoxy-5-nitro-4-phenylbenzoic acid is collected by filtration, washed with water and dried. It is saponified by heating with 4 N sodium hydroxide (250 ml) for 30 minutes; the resulting solution is left at 5° C for about 20 hours and is then filtered. The filtrate is acidified with 4 N hydrochloric acid to precipitate 3-hydroxy-5-nitro-4-phenylbenzoic acid. It is collected by filtration, washed with water and dried. After recrystallization from aqueous methanol, the acid is obtained with a melting point of 213°-215° C.

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture is refluxed for a further 4-5 hours
  3. customthe precipitated crude 3-acetoxy-5-nitro-4-phenylbenzoic acid
  4. filtrationis collected by filtration
  5. washwashed with water
  6. customdried
  7. temperatureby heating with 4 N sodium hydroxide (250 ml) for 30 minutes
  8. waitthe resulting solution is left at 5° C for about 20 hours
  9. filtrationis then filtered
  10. customto precipitate 3-hydroxy-5-nitro-4-phenylbenzoic acid
  11. filtrationIt is collected by filtration
  12. washwashed with water
  13. customdried
  14. customAfter recrystallization from aqueous methanol
  15. customthe acid is obtained with a melting point of 213°-215° C.

Sources & evidence

ORD record
ord-ccc2cdcdc79c4cd7990b0a59c97e41f8
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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