Benzene → 5-Chloro-1-phenyl-1-pentanone

HRID 1758291Notes

Reaction equation

HRID 1758291 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].Cl[CH:6]([CH3:12])[CH2:7][CH2:8][C:9](Cl)=[O:10].[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)(Cl)Cl>[C:13]1([C:9]([CH2:8][CH2:7][CH2:6][CH2:12][Cl:1])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 6451240Aluminum(III) ChlorideHCID 126039624-Chloropentanoyl chloride

Product 1

HCID 703385-Chloro-1-phenyl-1-pentanoneYield 42.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Aluminum chloride (16 g, 0.12 mol) is suspended in carbon tetrachloride (80 ml). To the suspension is added dropwise 4-chlorovaleric acid chloride (18.6 g, 0.12 mol) with ice-cooling. The mixture is stirred for 15 minutes and benzene (7.8 g, 0.1 mol) is added dropwise to the mixture at below 5° C. Stirring is continued at the same temperature for 1 hour. The mixture is poured into ice-hydrochloric acid and extracted with chloroform. The chloroform layer is washed with water, saturated aqueous sodium bicarbonate, water and then saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Chloroform is distilled off and the resulting crude crystals are recrystallized from hexane to obtain 4-chlorobutyl phenyl ketone (8.3 g) as colorless flakes, m.p. 49°-50° C.

Workup

  1. temperaturecooling
  2. stirringStirring
  3. waitis continued at the same temperature for 1 hour
  4. extractionextracted with chloroform
  5. washThe chloroform layer is washed with water, saturated aqueous sodium bicarbonate, water
  6. dry with materialsaturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  7. distillationChloroform is distilled off
  8. customthe resulting crude crystals are recrystallized from hexane

Sources & evidence

ORD record
ord-ba30d7d58a4542fe941cb8d0d88266ed
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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