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

HRID 1770116Notes

Reaction equation

HRID 1770116 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=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][CH2:2][CH2:3][CH2:4][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:18]

Participants

7

Reactant 5

HCID 111,2-Dichloroethane2×HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 78543(4-Chlorobutyl)benzeneHCID 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) 1-chloro-4-phenylbutane 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 separated, and the organic layer washed with 1N HCl, aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (delta, CDCl3): 1.76 (m, 4H), ~2.5 (s, 3H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR cm-1, neat): 1678 (C =O).

Workup

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

Sources & evidence

ORD record
ord-29b9ee8e8b8a4db6a3ba2d89b065938b
Source dataset
uspto-grants-1995_01
Patent number
US05385916

Reaction notes

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