Water → 1,1,7-TRICHLORO-1-HEPTEN-3-ONE

HRID 362660Notes

Reaction equation

HRID 362660 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:13][C:14]([Cl:16])=[CH2:15].O>C(Cl)Cl>[Cl:13][C:14]([Cl:16])=[CH:15][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6366Vinylidene chlorideHCID 740895-Chlorovaleryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 108568781,1,7-TRICHLORO-1-HEPTEN-3-ONE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

100 g (0.62 mol) 5-Chlorovaleroyl chloride was added dropwise to 78.53 g (0.589 mmol) aluminium chloride in 150 ml methylene chloride at room temperature. After stirring for 1 hour, 45 ml (0.558 mol) 1,1-dichloroethylene in 25 ml methylene chloride was added dropwise. Under ice-cooling 100 ml water was added dropwise and solid material suction filtered on Celite. The filtrate was washed with water and the organic phase dried and concentrated. The residue was distilled in a rotary evaporator.

Workup

  1. additionwas added dropwise
  2. filtrationsolid material suction filtered on Celite
  3. washThe filtrate was washed with water
  4. customthe organic phase dried
  5. concentrationconcentrated
  6. distillationThe residue was distilled in a rotary evaporator

Sources & evidence

ORD record
ord-28f460e647064d609373f3b7abc6c5b6
Source dataset
uspto-grants-1999_02
Patent number
US05869686

Reaction notes

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