Hydrochloric Acid → 1-Pentanone, 1-[1,1'-biphenyl]-4-yl-

HRID 328307Notes

Reaction equation

HRID 328307 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl.[OH2:6].[N+]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-])=O>>[C:12]([C:10]1[CH:15]=[CH:14][C:13]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:12][CH:11]=1)(=[O:6])[CH2:11][CH2:10][CH2:15][CH3:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7416Nitrobenzene2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 30848821-Pentanone, 1-[1,1'-biphenyl]-4-yl-Yield 95%

Procedure

560 Gram of granular anhydrous aluminum chloride and 1 l of nitrobenzene were introduced into a 5 l three neck flask, and stirred under water-cooling to give a solution. A solution of 600 g of diphenyl and 482.5 g of n-valeric acid chloride dissolved in 1 l of nitrobenzene (prepared in advance) was dropwise added into said three neck flask over 2 hours. After the addition, the resulting mixture was stirred for one hour as it was. Thereafter it was stirred at 40°-45° C for 2 hours, cooled to room temperature, poured cautiously into a mixed solution of 1.3 l of conc. hydrochloric acid and 1.5 l of water for decomposing the catalyst, and cooled to 20° C. Precipitated crystal was separated by filtration. Nitrobenzene was distilled off from nitrobenzene layer by distillation under a reduced pressure to give an additional crystal. Both the crystals were recrystallized from ethanol to give 881 g of crystal of 4-n-pentanoylbiphenyl (m.p. 79°-79.5° C) (yield: 95% based on biphenyl).

Workup

  1. temperaturecooling
  2. customto give a solution
  3. additionwas dropwise added
  4. customover 2 hours
  5. additionAfter the addition
  6. stirringthe resulting mixture was stirred for one hour as it
  7. stirringThereafter it was stirred at 40°-45° C for 2 hours
  8. temperaturecooled to 20° C
  9. customPrecipitated crystal
  10. customwas separated by filtration
  11. distillationNitrobenzene was distilled off from nitrobenzene layer by distillation under a reduced pressure
  12. customto give an additional crystal
  13. customBoth the crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-785a0e54d7a9408d8aa593d368653300
Source dataset
uspto-grants-1977_04
Patent number
US04017416

Reaction notes

Loading…