Hydrochloric Acid → (2-Chloro-4-nitrophenyl)(phenyl)methanone

HRID 1288408Notes

Reaction equation

HRID 1288408 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O.Cl.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[Cl:5][C:6]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:7]=1[C:8]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 74482-Chloro-4-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 884819(2-Chloro-4-nitrophenyl)(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Thionyl chloride (35.8 grams, 0.305 mole) was added to a benzene solution of 2-chloro-4-nitrobenzoic acid (60.3 grams, 0.3 mole) and the mixture heated to reflux during 5 hours until the evolution of hydrogen chloride had ceased. Aluminum chloride (100 grams, 0.72 mole) was added slowly to the stirred solution during a 3.5 hour period and the temperature rose to 48° C. After the addition, the mixture was warmed to 80° C. for 2 hours, cooled, poured onto ice-water (one liter), concentrated hydrochloric acid (90 ml.) added and the mixture warmed at 40° C. for 3 hours. Benzene extraction followed by successive treatment with 5% aqueous sodium hydroxide, water and calcium chloride yielded, after removal of benzene, a reddish black residue purified by filtration. The pale yellow solid so obtained was further characterized as having a melting point equal to 95.5° - 96.5° C. in 44% yields.

Workup

  1. temperaturethe mixture heated
  2. customrose to 48° C
  3. additionAfter the addition
  4. temperaturecooled
  5. additionadded
  6. temperaturethe mixture warmed at 40° C. for 3 hours
  7. extractionBenzene extraction
  8. customyielded
  9. customafter removal of benzene
  10. filtrationa reddish black residue purified by filtration
  11. customThe pale yellow solid so obtained
  12. customequal to 95.5° - 96.5° C.
  13. customyields

Sources & evidence

ORD record
ord-6ae68da32b8f4423b7b6328c5ce6c40a
Source dataset
uspto-grants-1976_10
Patent number
US03988300

Reaction notes

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