Vinyl Chloride → 1,1,3,3-Tetrachloropropane-1-phosphonic dichloride

HRID 1438897Notes

Reaction equation

HRID 1438897 reaction equation
[CH:1]([Cl:3])=[CH2:2].[Cl:4][C:5]([Cl:11])(Cl)[P:6]([Cl:9])([Cl:8])=[O:7].[Cl-:12].C([NH+](CC)CC)C>C(#N)C.C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1>[Cl:4][C:5]([Cl:11])([P:6]([Cl:9])([Cl:8])=[O:7])[CH2:2][CH:1]([Cl:12])[Cl:3]

Participants

6

Reactant 3

HCID 6338Vinyl ChlorideHCID 277422(Trichloromethyl)phosphonic dichlorideHCID 12698378Triethylazanium chloride

Product 1

HCID 213996861,1,3,3-Tetrachloropropane-1-phosphonic dichlorideYield 27.8%

Reagents, catalysts & solvents 2

HCID 8400BenzoinCatalystHCID 6342AcetonitrileSolvent

Procedure

6.25 g (0.1 mole) vinyl chloride, 23.6 g (0.1 mole) trichloromethane phosphonic dichloride, 540 mg (2 mmole) ferric chloride hexahydrate, 412 mg (3 mole) triethylammonium chloride, and 424 mg (2 mmole) benzoin were heated in 30 ml acetonitrile in an ampoule at 100° during 15 hours. After opening of the ampoule, and evaporating unconverted vinyl chloride, the reaction product was diluted with methylene chloride, washed twice with ice-cold 1N aqueous hydrochloric acid and dried on calcium chloride. The solvent was distilled at atmospheric pressure, and unconverted phosphonic dichloride sublimed at 25 mm and120°. The remainder was fractionated in vacuo, giving 8.3 g 1,1,3,3-tetrachloropropane-1-phosphonic dichloride, bp/0.1: 66° -67°; containing 70.3% Cl (Calc. for C3H3Cl6OP: 71.0%).

Workup

  1. customevaporating unconverted vinyl chloride
  2. additionthe reaction product was diluted with methylene chloride
  3. washwashed twice with ice-cold 1N aqueous hydrochloric acid
  4. customdried on calcium chloride
  5. distillationThe solvent was distilled at atmospheric pressure, and unconverted phosphonic dichloride

Sources & evidence

ORD record
ord-e3eaeb2c5b7e4e6ca9cb6186fd085ac5
Source dataset
uspto-grants-1977_11
Patent number
US04057578

Reaction notes

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