Dichloromethane → 1.1,3-Trichloropentane-1-phosponic dichloride

HRID 1438896Notes

Reaction equation

HRID 1438896 reaction equation
[CH3:1][CH2:2][CH:3]=[CH2:4].[Cl:5][C:6]([Cl:12])(Cl)[P:7]([Cl:10])([Cl:9])=[O:8].C(Cl)[Cl:14]>C1C(C(OOC(C)(C)C)=O)=CC=CC=1>[Cl:5][C:6]([Cl:12])([P:7]([Cl:10])([Cl:9])=[O:8])[CH2:4][CH:3]([Cl:14])[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 78441-ButeneHCID 277422(Trichloromethyl)phosphonic dichloride

Product 1

HCID 213996821.1,3-Trichloropentane-1-phosponic dichloride

Reagents, catalysts & solvents 1

HCID 11966tert-Butyl peroxybenzoateCatalyst

Procedure

5.6 g (0.1 mole)butene-1, 71 g (0.3 mole) trichloromethane phosphonic dichloride and 0.5 g tert. butyl perbenzoate were heated in 100 ml methylene chloride in a closed ampoule and in the absence of air, during 10 hours at 120°. After cooling, the ampoule was opened and its contents distilled. Unconverted trichloromethane phosphonic dichloride sublimed between 70° and 125° at 25 mm pressure. The continued distillation yielded 10.3 g 1.1,3-trichloropentane-1-phosphonic dichloride, bp/0.05: 64° -66°. Found Cl: 61.3% Calc. for C5H8Cl5OP: 61.0%.

Workup

  1. temperatureAfter cooling
  2. distillationits contents distilled
  3. customUnconverted trichloromethane phosphonic dichloride sublimed between 70° and 125°
  4. distillationThe continued distillation

Sources & evidence

ORD record
ord-334bc9acc5b949f38fb2d8fab1a5612a
Source dataset
uspto-grants-1977_11
Patent number
US04057578

Reaction notes

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