Hydrochloric Acid → 1-(4'-Pentyl-1,1'-biphenyl-4-yl)ethanone

HRID 328309Notes

Reaction equation

HRID 328309 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH2:8][CH3:9].[C:22](Cl)(=[O:24])[CH3:23].Cl>[N+](C1C=CC=CC=1)([O-])=O.O>[CH2:5]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([C:22](=[O:24])[CH3:23])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 815464-PentylbiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 52444161-(4'-Pentyl-1,1'-biphenyl-4-yl)ethanoneYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7416NitrobenzeneSolvent2×

Procedure

392 Gram of granular anhydrous aluminum chloride and 700 ml of nitrobenzene were introduced into 5 l three neck flask, and dissolved with stirring. A solution of 600 g of 4-n-pentylbiphenyl and 220 g of acetyl chloride dissolved in 500 ml of nitrobenzene (prepared in advance) was dropwise added to said three neck flask over 1 hour, followed by stirring for one hour, further stirring at 40°-45° C for 2 hours, cooling to room temperature, pouring cautiously into a mixed liquid of 250 ml of conc. hydrochloric acid and 1.25 l of water, distilling off nitrobenzene from nitrobenzene layer by distillation under a reduced pressure, separating the resulting solid by filtration, and recrystallizing it from ethanol, to give 597 g of 4'-n-pentyl-4-acetylbiphenyl (m.p. 81°-82°) (Yield 84%).

Workup

  1. dissolutiondissolved
  2. additionwas dropwise added
  3. customover 1 hour
  4. stirringby stirring for one hour
  5. stirringfurther stirring at 40°-45° C for 2 hours
  6. distillationdistilling off nitrobenzene from nitrobenzene layer
  7. distillationby distillation under a reduced pressure
  8. customseparating the resulting solid
  9. filtrationby filtration
  10. customrecrystallizing it from ethanol

Sources & evidence

ORD record
ord-1b81a0e39c8a4427948c537f02eeb995
Source dataset
uspto-grants-1977_04
Patent number
US04017416

Reaction notes

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