1,2-Dichloroethane → 6-Chloro-1-phenyl-1-hexanone

HRID 329417Notes

Reaction equation

HRID 329417 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=[O:18])C.Cl.[Cl:21][CH2:22][CH2:23]Cl>O>[Cl:21][CH2:22][CH2:23][CH2:11][CH2:10][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)=[O:18]

Participants

7

Reactant 5

HCID 111,2-Dichloroethane2×HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 524314Benzene, 1-butyl-4-chloro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 41827306-Chloro-1-phenyl-1-hexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 4-chlorophenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers were separated, and the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (CDCl3): 1.76 (m, 4H), 2.54 (m, 3H), 2.66 (m, 2H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR (cm.-1, neat): 1678 (C=O).

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to an oil, 6.7 g (>100%)

Sources & evidence

ORD record
ord-c3c87cd6018c40d085f2e809619b2abc
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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